Category: 152626-77-2

Kermack, Wm. O.; Wight, Thomas W. published an article in 1935, the title of the article was Attempts to find new antimalarials. XIV. Derivatives of 8-methylquinoline.Product Details of 152626-77-2 And the article contains the following content:

cf. C. A. 29, 7332.6. 5,2-MeO(Me)C6H3NH2, FeSO4, As2O5 and 96% H2SO4, refluxed 4 hrs., give 6-methoxy-8-methylquinoline (I), whose HBr salt, light yellow, m. 268°, and picrate, yellow, m. 232-3°. I in CHCl3, saturated with HBr and treated with Br, gives the 5-Br derivative, m. 116-17° (HBr salt, light yellow, m. 230°). 6-Nitro-m-cresol and Br in CHCl3 give the 4-Br derivative, m. 146°; Me2SO4 and K2CO3 in C6H6 give 4-bromo-6-nitro-m-tolyl Me ether, m. 110-11°; reduction with Fe in concentrated HCl in MeOH gives 4-bromo-5-methoxy-o-toluidine (II), light pink, m. 79-80°; the diazo reaction with CuBr yields 4,6-dibromo-m-tolyl Me ether, m. 73-4°. 6-Bromo-4-nitro-m-tolyl Me ether (III) m. 113-15° (90% yield); reduction gives 90% of 2-bromo-5-methoxy-p-toluidine, m. 71-3° (Ac derivative, m. 130-3°); the Sandmeyer reaction gives III. II with the Skraup reaction gives the 5-Br derivative of I; the 7-Br derivative of I m. 134-5°. 6-Nitro-8-methylquinoline yields a 3-Br derivative, light yellow, m. 188-9°. 8-Bromomethylquinoline, refluxed overnight with N H2SO4, gives 8-quinolylmethyl alc., m. 75-6°; 5-NO2 derivative, light brown, m. 148-9°. 5-Nitro-8-bromomethylquinoline and piperidine in Et2O give the 8-piperidinomethyl derivative, whose HBr salt m. 248-9°. o-O2NC6H4CH2NHEt, Et2NCH2CH2Cl.HCl (IV), K2CO3 and a trace of Cu bronze in C6H6, refluxed 4 hrs., give β-(o-nitrobenzylethylamino)triethylamine (V), whose picrate, light yellow, m. 167-8°; o-NH2 derivative, as the picrate, light yellow, m. 134°; β-(benzylethylamino)-triethylamine picrate, yellow, m. 150-2°. The p-NO2 isomer of V, as the picrate, yellow, m. 195-7°. PrNH2 and IV give β-diethylaminoethylpropylamine, whose picrate, yellow, m. 133-5°; butylamine analog, b. 207-12° (70% yield) (dipicrate, yellow, m. 234°); isobutylamine analog, b. 194-200° (70% yield) (dipicrate, yellow, m. 141°); the following piperidino compounds were analogously prepared; the dipicrates form yellow plates; β-piperidinoethylpropylamine, b. 220-30°, 60% yield (dipicrate, m. 169°); -butylamine, b. 230-40°, 70% (dipicrate, m. 191-2°); -isobutylamine, b. 230-40°, 70% (dipicrate, m. 167-8°); -methylamine, b. 190-200°, 45% (dipicrate, m. 174°); β-piperidinodiethylamine, b. 200-10°, 55% (dipicrate, m. 154°). C2H4Br2 and MeNH2 in EtOH give 50% of sym-dimethylethylenediamine, b. 150-60° (picrate, m. 160°). 8-Bromomethylquinoline and Et2NCH2CH2NHMe with K2CO3 in C6H6 give 8-(β-diethylaminoethylmethylaminomethyl)quinoline, the tri-HBr salt of which m. 215-16°; β-diethylaminodiethylaminomethyl derivative (tri-HBr salt, m. 218-19°; picrate, yellow, m. 131-2°); β-diethylaminoethylpropylaminomethyl derivative (picrate, light yellow, m. 113-15°; dipicrate, deep yellow, m. 163-4°); diethylaminoethylbutylaminomethyl derivative (dipicrate, yellow, m. 178-80°); β-diethylaminoethylisobutylaminomethyl derivative (dipicrate, deep yellow, m. 169-71°); β-piperidinoethylpropylaminomethyl derivative (tri-HBr salt, m. 210°); butylamino analog, m. 211-12°; isobutylamino analog (dipicrate, yellow, m. 210-11°); methylamino analog (dipicrate, yellow, m. 205-6°); β-piperidinodiethylaminomethyl derivative (tri-HBr salt, m. 222°); sym-bis(8-quinolylmethyl)dimethylethylenediamine di-HBr, m. 232°. Bis(8-quinolylmethyl)-β-diethylaminoethylamine, m. 97-8°; picrate, yellow, m. 191°; 8-(β-diethylaminoethylaminomethyl)quinoline tri-HBr, m. 223-4°. 1-β-Bis(8′-quinolylmethyl)aminoethylpiperidine, m. 97-8°; picrate, pale yellow, m. 228-9°. 1,4-Bis(8′-quinolylmethyl)piperazine, with 0.5 mol. H2O, m. 153-4°; HBr salt, m. 265-7°. Although inactive in bird malaria, some of these compounds possess marked local anesthetic activity. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Product Details of 152626-77-2

4-Bromo-5-methoxy-2-methylaniline(cas:152626-77-2) belongs to ethers. Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. Product Details of 152626-77-2

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Griffith, R. H.; Hope, Edward published an article in 1925, the title of the article was Synthesis of 5,5′-dibromo-6,6′-dimethoxy-2,2′-bisoxythionaphthene.HPLC of Formula: 152626-77-2 And the article contains the following content:

5-Bromo-2-acetylamino-p-tolyl Me ether (I), m. 191°; hydrolysis with concentrated HCl gives the amine, m. 100° (Bz derivative, m. 159°); the azo dye with β-C10H7OH, red needles with green luster, m. 210°. Diazotized and reduced with SnCl4, the amine gives a hydrazine, pale brown, m. 192°, which, on treatment with CuSO4 and oxidation with alk. KMnO4, yields 3-bromoanisic acid, m. 217-8°. Since the 2-Br derivative is recorded as m. 212°, it was synthesized from 2-bromo-p-tolyl Me ether, b16 114° b760 222°, and found to m. 199°. Oxidation of I with KMnO4 in the presence of MgSO4 gives about 70% of 5-bromo-2-acetylamino-4-methoxybenzoic acid, m. 253°; hydrolysis with concentrated HCl gives 4-bromo-m-anisidine, m. 90.5° (Bz derivative m. 124°); hydrolysis with alkali gives 5-bromo-2-amino-4-methoxy-benzoic acid, pale brown, m. 201°, decomposed 213° (Na salt, long needles; Cu salt, green). Diazotized, treated with Na2S2 and boiled with Zn dust in Na2CO3 solution, it yields 5-bromo-4-methoxy-2-thiolbenzoic acid, which, because of its ease of oxidation, is used as the Na salt in the condensation with ClCH2CO2H, forming 4-bromo-2-carboxy-5-methoxy-phenylthiolacetic acid (II), pale brown, m. 243° (decomposition). Heated with AcONa and Ac2O, dissolved in 3% alkali and treated with K3Fe(CN)6, it gives 5,5′-dibromo-6,6′-dimethoxy-2,2′-bisoxythionaphthene (III), dark red, m. 355-60°; the dye is reprecipitated from its deep blue solution in concentrated H2SO4 in a gelatinous state very suitable for the preparation of the vat, which is pale yellow and dyes cloth a good scarlet. The PhNO2 solution shows an absorption band with a maximum at λ = 529; “Helindone Fast Scarlet R” shows a similar band with a maximum at λ = 520. II and isatin give the compound C17H10O3N-BrS (IV), which has a much bluer shade than III; its H2SO4 solution is purple but its dyeing properties are unsatisfactory, probably on account of further reaction during reduction. II and acenaphthenequinone give an orange powder (V), m. 337°, giving dark brown solutions in concentrated H2SO4 and dyeing cloth a good orange from a bright blue bath. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).HPLC of Formula: 152626-77-2

4-Bromo-5-methoxy-2-methylaniline(cas:152626-77-2) belongs to ethers. Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. HPLC of Formula: 152626-77-2

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Ether – Wikipedia,
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On June 22, 2017, Weiss, Matthias; Gagnepain, Julien Daniel Henri; Hoffman, Thomas James; Sulzer-Mosse, Sarah; Lamberth, Clemens published a patent.Name: 4-Bromo-5-methoxy-2-methylaniline The title of the patent was Microbiocidal phenylamidine derivatives for combating, preventing or controlling phytopathogen infestation of plants. And the patent contained the following:

Compounds of the formula (I) wherein R1 and R2 are each independently selected from C1-C4-alkyl and C3-C8-cycloalkyl; or together with nitrogen atom to which they are attached form a three to six-membered saturated cyclic group which may optionally contain one oxygen or one sulfur atom; R3 is hydrogen, halogen or C1-C4-alkyl; R4 is C1-C4-alkyl or C1-C4-haloalkyl; R5 and R6 are each independently selected from C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, etc.; R8 is selected from hydrogen, C1-C4-alkyl, C1-C4-alkoxy and C3-C8-cycloalkyl; and X is NR8, O or S; or a salt or an N-oxide thereof. Furthermore, the present invention relates to agrochem. compositions which comprise compounds of formula I, to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Name: 4-Bromo-5-methoxy-2-methylaniline

The Article related to fungicide phenylamidine derivative preparation phytopathogenic fungi crop, Agrochemical Bioregulators: Invertebrate and other aspects.Name: 4-Bromo-5-methoxy-2-methylaniline

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On June 26, 2014, Rooney, Lisa; Vidal, Agnes; D’Souza, Anne-Marie; Devereux, Nick; Masick, Brian; Boissel, Valerie; West, Ryan; Head, Victoria; Stringer, Rowan; Lao, Jianmin; Petrus, Matt J.; Patapoutian, Ardem; Nash, Mark; Stoakley, Natalie; Panesar, Moh; Verkuyl, J. Martin; Schumacher, Andrew M.; Petrassi, H. Michael; Tully, David C. published an article.Computed Properties of 152626-77-2 The title of the article was Discovery, Optimization, and Biological Evaluation of 5-(2-(Trifluoromethyl)phenyl)indazoles as a Novel Class of Transient Receptor Potential A1 (TRPA1) Antagonists. And the article contained the following:

A high throughput screening campaign identified 5-(2-chlorophenyl)indazole as an antagonist of the transient receptor potential A1 (TRPA1) ion channel with IC50 = 1.23 μM. Hit to lead medicinal chem. optimization established the SAR around the indazole ring system, demonstrating that a trifluoromethyl group at the 2-position of the Ph ring in combination with various substituents at the 6-position of the indazole ring greatly contributed to improvements in vitro activity. Further lead optimization resulted in the identification of compound I, a potent and selective antagonist of TRPA1 in vitro (IC50 = 0.015 μM), which has moderate oral bioavailability in rodents and demonstrates robust activity in vivo in several rodent models of inflammatory pain. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Computed Properties of 152626-77-2

The Article related to fluoromethylphenyl indazole transient receptor potential a1 ion channel antagonist, trpa1 antagonist discovery optimization sar analgesic, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Computed Properties of 152626-77-2

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On August 10, 2021, Doi, Hisashi; Watanabe, Yasuyoshi; Choi, Yilong; Kida, Tatsuya; Tateishi, Ukihide; Kano, Daisuke; Mori, Shigeyuki; Mori, Yasuo; Uesugi, Motonari published a patent.Synthetic Route of 152626-77-2 The title of the patent was Preparation of thiazole and indazole derivatives for visualizing TRPA1. And the patent contained the following:

The present invention provides thiazole and indazole derivatives I and II [R1 = a substituent having a radioisotope; R2 = a substituent having a radioisotope] or their salts for visualizing TRPA1 (transient receptor potential ankyrin 1) in vivo. For example, compound III (preparation given) was reacted with [11C]methyl triflate (11CH3OTf, preparation given) to provide compound IV. According to the present invention, it is possible to provide a technol. for visualizing TRPA1 in vivo. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Synthetic Route of 152626-77-2

The Article related to thiazole indazole derivative preparation trpa1 visualization bioimaging agent radioisotope, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Synthetic Route of 152626-77-2

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On August 22, 1995, James, Donald R.; Baker, Don R.; Mielich, Steven D.; Michaely, William J.; Fitzjohn, Steven; Knudsen, Christopher G.; Mathews, Christopher; Gerdes, John M. published a patent.Application In Synthesis of 4-Bromo-5-methoxy-2-methylaniline The title of the patent was Aryl indazoles, a process for producing them, and their use as herbicides. And the patent contained the following:

This invention relates to substituted arylindazoles I (R1 = H or halo; R2 = e.g., N, nitro, halo; R3 = e.g., H, halo; R4, R5, R6 are independently, e.g., H, halo, nitro, hydroxy, cyano; R7 = H, halo, C1-6 alkyl, nitro; R8 = H, halo), a process for producing them and their use as herbicides. Thus, e.g., 5-methoxy-2-methyl-4-nitroaniline was converted to 6-methoxy-5-nitroindazole by standard diazotization-cyclization route; arylation of the latter with 3,5-dichloro-4-fluorobenzotrifluoride afforded the 1-arylindazole I (R1-R8, X given resp. as: H, Cl, CF3, H, NO2, OMe, H, H, C-Cl) which exhibited 100% control pre-emergence of green foxtail, watergrass, wild mustard, and velvetleaf, and 100% control post-emergence of green foxtail, wild mustard, and velvetleaf. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Application In Synthesis of 4-Bromo-5-methoxy-2-methylaniline

The Article related to arylindazole herbicide, indazole aryl herbicide, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Application In Synthesis of 4-Bromo-5-methoxy-2-methylaniline

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Ether – Wikipedia,
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On January 7, 2010, Marsilje, Thomas H., III; Lu, Wenshuo; Chen, Bei; He, Xiaohui; Lee, Christian Cho-Hua; Jiang, Songchun; Yang, Kunyong published a patent.Synthetic Route of 152626-77-2 The title of the patent was Preparation of substituted 2-(phenylamino)pyrimidin-4-amine as IGF-1 receptor and anaplastic lymphoma kinase inhibitors for treating proliferative disorders. And the patent contained the following:

The invention is related to the preparation of pyrimidine derivatives I [ring E may optionally contain a double bond; one of Z1-3 = NR6, N(R6)(:O) or S(O)1-2 and the others are CR2; R6 = H, azetidin-3-yl, 1,1-dioxo-2H-thiopyran-4-yl,, (un)substituted alk(en/yn)yl, 4-(pyrrolidin-1-yl)-1-oxobutyl, 3-morpholinopropylsulfonyl, etc.; R2 = (un)substituted 2-oxo-1,2-dihydropyridin-3-yl, 2-oxoazepan-3-yl, 5-6 membered heteroaryl containing 1-3 heteroatoms selected from N, O and S; R1 = halo, optionally halogenated alkyl; R3, R4 = H; R5 = halo, OH, alkyl, alkoxy, CN, etc.; X = Y = (CH)0-1; m = 2-4] and their physiol. acceptable salts which may be used to treat, ameliorate or prevent a condition which responds to inhibition of insulin-like growth factor (IGF-1R) or anaplastic lymphoma kinase (ALK), and to their pharmaceutical compositions Thus, monoamination of 2,5-dichloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (preparation given) with tert-Bu 4-(4-amino-5-fluoro-2-methylphenyl)piperidine-1-carboxylate (preparation given) and reductive amination of formaldehyde gave II. Selected I had IC50 values in the range of 1 nM – 1 μM for the inhibition of IGF-1R. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Synthetic Route of 152626-77-2

The Article related to phenylaminopyrimidineamine preparation igf1r anaplastic lymphoma kinase inhibitor antiproliferative neoplasm, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Synthetic Route of 152626-77-2

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Malik, Qasim M.; Ijaz, Sadia; Craig, Donald C.; Try, Andrew C. published an article in 2011, the title of the article was Synthesis and reactivity of dimethoxy-functionalized Troeger’s base analogs.Recommanded Product: 4-Bromo-5-methoxy-2-methylaniline And the article contains the following content:

Troeger’s base analogs were prepared bearing methoxy groups in the 1,7-, 2,8-, 3,9- or 4,10-positions. These compounds were converted to their dihydroxy analogs in excellent yields upon treatment with boron tribromide and the 4,10-dihydroxy analog could be prepared by directly from 4-hydroxyaniline. The synthetic utility of the dihydroxy-functionalized compounds as building blocks was demonstrated by the synthesis of a dialkoxy and a diester Troeger’s base analog. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Recommanded Product: 4-Bromo-5-methoxy-2-methylaniline

The Article related to troeger base dihydroxy preparation alkylation acylation, Heterocyclic Compounds (More Than One Hetero Atom): Eight- and Higher-Membered Rings and other aspects.Recommanded Product: 4-Bromo-5-methoxy-2-methylaniline

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Ether – Wikipedia,
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On March 17, 2016, Nagamochi, Masatoshi; Gotanda, Kentoku; Noguchi, Tetsuji; Goto, Taiji; Sasaki, Junko; Torihata, Munefumi; Yoshino, Toshiharu; Isobe, Takashi; Ramadass, Venkataramanan published a patent.Recommanded Product: 4-Bromo-5-methoxy-2-methylaniline The title of the patent was Preparation of carboxylic acid derivatives as RORγt (retinoic acid receptor-related orphan receptor γt) inhibitors. And the patent contained the following:

Title compounds I [R1 = alkyl, cycloalkyl or phenyl; R2 = H, halo, alkyl, etc.; R3 = H, carboxy-alkyl or hydroxy; R4 = halo or alkyl; R5 = H or alkyl; R6 = H, halo or alkyl; R7 = H, halo, alkyl, etc.; R8 = hydroxy, alkoxy, monoalkylamino, etc.; L = single bond, methylene or oxygen atom; E = phenylene (optionally substituted with halo, alkyl or alkylsulfonyl), pyridinylene (optionally substituted with halo, alkyl or alkylsulfonyl), thienylene, etc.; Q1 = nitrogen atom or CH; Q2 = nitrogen atom or CH; -U-T- = -CH2CH2- or -CH:CH-; Y = methylene or oxygen atom; V = nitrogen atom or C(R9); R9 = H, alkyl, cycloalkyl, etc.; or pharmaceutically acceptable salts thereof], useful for the treatment of psoriasis, psoriatic arthritis, etc., were prepared For example, EDCI-mediated amidation of II [R = OH] (prepared from 1-bromo-4-iodo-2-methylbenzene in a multi-step process) with methylamine·HCl afforded compound II [R = NHMe]. In IL-17 production inhibition assay, 81-example of I showed IC50 values (nM) ranging from 4.48 to 1110, e.g., IC50 of II [R = NHMe] was 4.48 nM. Pharmaceutical compositions comprising I are disclosed. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Recommanded Product: 4-Bromo-5-methoxy-2-methylaniline

The Article related to carboxylic acid preparation ror gamma t inhibitor, psoriasis psoriatic arthritis treatment ror gamma t inhibition, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Recommanded Product: 4-Bromo-5-methoxy-2-methylaniline

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

On March 17, 2016, Nagamochi, Masatoshi; Gotanda, Kentoku; Noguchi, Tetsuji; Goto, Taiji; Sasaki, Junko; Torihata, Munefumi; Yoshino, Toshiharu; Isobe, Takashi; Ramadass, Venkataramanan published a patent.Recommanded Product: 4-Bromo-5-methoxy-2-methylaniline The title of the patent was Preparation of carboxylic acid derivatives as RORγt (retinoic acid receptor-related orphan receptor γt) inhibitors. And the patent contained the following:

Title compounds I [R1 = alkyl, cycloalkyl or phenyl; R2 = H, halo, alkyl, etc.; R3 = H, carboxy-alkyl or hydroxy; R4 = halo or alkyl; R5 = H or alkyl; R6 = H, halo or alkyl; R7 = H, halo, alkyl, etc.; R8 = hydroxy, alkoxy, monoalkylamino, etc.; L = single bond, methylene or oxygen atom; E = phenylene (optionally substituted with halo, alkyl or alkylsulfonyl), pyridinylene (optionally substituted with halo, alkyl or alkylsulfonyl), thienylene, etc.; Q1 = nitrogen atom or CH; Q2 = nitrogen atom or CH; -U-T- = -CH2CH2- or -CH:CH-; Y = methylene or oxygen atom; V = nitrogen atom or C(R9); R9 = H, alkyl, cycloalkyl, etc.; or pharmaceutically acceptable salts thereof], useful for the treatment of psoriasis, psoriatic arthritis, etc., were prepared For example, EDCI-mediated amidation of II [R = OH] (prepared from 1-bromo-4-iodo-2-methylbenzene in a multi-step process) with methylamine·HCl afforded compound II [R = NHMe]. In IL-17 production inhibition assay, 81-example of I showed IC50 values (nM) ranging from 4.48 to 1110, e.g., IC50 of II [R = NHMe] was 4.48 nM. Pharmaceutical compositions comprising I are disclosed. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Recommanded Product: 4-Bromo-5-methoxy-2-methylaniline

The Article related to carboxylic acid preparation ror gamma t inhibitor, psoriasis psoriatic arthritis treatment ror gamma t inhibition, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Recommanded Product: 4-Bromo-5-methoxy-2-methylaniline

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Ether – Wikipedia,
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