Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1663-61-2, Safety of (Triethoxymethyl)benzene

b. 1-Azidoethyl-2,4-dibenzoylmannose To a 1.0 L, 3-neck flask containing a stir bar, nitrogen inlet and 300 mL of anhydrous acetonitrile was added 25 gm 1-azidoethylmannose (100.4 mmole), and 50 mL triethyl orthobenzoate (220 mmole, 2.2 equiv.). The resulting slurry was stirred at room temperature and 0.8 mL (10 mmole) trifluoroacetic acid (TFA) was added neat. The solution cleared within 10 minutes and stirring was continued for an additional two hours, then 25 mL of 10percent aqueous TFA was added and stirring was continued for an additional 2 hours to hydrolyze the intermediate to the ester isomers. The solvent was evaporated under vacuum to a viscous oil, which was triturated with 50 mL DCM and again evaporated to a viscous oil. Toluene (70 mL) was added to the residue and the viscous solution was seeded with 2,4-dibenzoylazidoethylmannose. A fine precipitate formed within 15 minutes and stirring was continued overnight at room temperature. The resulting heavy suspension was set in the freezer for 2-4 hours, then filtered and the solid washed with ice cold toluene (2*10 mL). The solid was air dried to a constant weight to give 21 gm (TY 22.85 gm 50percent isomeric purity) of ?95percent isomeric purity. The product was taken into 40 mL toluene, stirred for 1 hour and then set in the freezer for an additional 2 hours. The solid was filtered and washed (2*10 mL) with ice cold toluene and air dried to a constant weight to give 18.5 gm of the single isomer product 2,4-dibenzoylazidoethylmannose in 83percent yield. The mother liquors contained the undesired isomer and a small amount of the desired isomer. The reaction was monitored by TLC: SG (Hexane/Ethyl Acetate 7/3) Starting Material Rf 0.0, orthoester intermediate Rf 0.9. (Hexane/Ethyl Acetate: 8/2) SM Rf 0.8, desired isomer Rf 0.4, un-desired isomer Rf 0.2 1H NMR 300 MHz (CDCl3) delta 8.12 (t, 4H), 7.66 (t, 2H), 7.5 (m, 4H), 5.56 (t, 1H), 5.48 (m, 1H), 5.14 (m 1H), 4.5 (dd, 1H), 4.0 (m, 2H), 3.8 (m, 3H), 3.56 (m, 1H), 3.44 (m, 1H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SMARTCELLS, INC.; Chen, Zhiyu; Lancaster, Thomas M.; Zion, Todd C.; US2013/190475; (2013); A1;,
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Reference of 1484-26-0, These common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred solutionof 3-(benzyloxy)aniline 10b (1.0 equiv.) in ethylformate (3 mL),catalytic amount of pTsOH monohydrate was added. The reactionmixture was stirred at rt for 3 days and the resulting mixture wasextracted with ethyl acetate. Organic layers were collected, washedwith water and brine, dried over anhydrous MgSO4 and evaporatedgiving the product 11b as white solid in 80percent yield.xNMR: mixture of two rotamers (approx. 1:1) 1H (600 MHz,CDCl3): d 8.67 (d, J 10.0 Hz, 1H), 8.32 (s, 1H), 7.97e7.67 (m, 22H),5.05 (s, 2H), 5.03 (s, 2H).

Statistics shows that 3-Benzyloxyaniline is playing an increasingly important role. we look forward to future research findings about 1484-26-0.

Reference:
Article; Surmiak, Ewa; Neochoritis, Constantinos G.; Musielak, Bogdan; Twarda-Clapa, Aleksandra; Kurpiewska, Katarzyna; Dubin, Grzegorz; Camacho, Carlos; Holak, Tad A.; Doemling, Alexander; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 384 – 407;,
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Related Products of 929-75-9, A common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure for the preparation of compounds 10-15 (B) (0016) The appropriate diamines were added to compound 1a and Na2CO3 (2eq.) with stirring in DMF (5mL). The mixture was stirred overnight at room temperature. After completion, as judged by TLC, the solvent was evaporated under reduced pressure. The mixture was resolved in EtOAc and washed twice with water and brine. The organic layer was dried over Na2SO4, then filtered and concentrated. The crude product was purified by column chromatography (CH2Cl2/MeOH, 25/1 v/v) to give the target compound as a white solid.

The synthetic route of 929-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Fei; Peng, Yiyun; Wang, Qi; Shi, Yongying; Si, Longlong; Wang, Han; Zheng, Yongxiang; Lee, Emily; Xiao, Sulong; Yu, Maorong; Li, Yingbo; Zhang, Chuanling; Tang, Hengli; Wang, Chunguang; Zhang, Lihe; Zhou, Demin; European Journal of Medicinal Chemistry; vol. 77; (2014); p. 258 – 268;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H8F3NO

General procedure: 5.3g (0.02 mol) of methyl N-nitro-1,3-dioxoisoindoline-2-carbimidothioate (3) was dissolved in 120 mL of acetonitrile, and cooled to 0-5, dropped in a quantity of 0.02 mmol of (aryl)methanamine over 5 mins. The reaction was stirred at 0-5 for one hour again. The mixture was filtered, concentrated in vacuo and recrystallised in EtOAc – petroleum ether (1:1) to give pure products 4a~4f.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Qinglai; Zhao, Fenghai; Zhu, Xiang; Zhou, Ziyuan; Yang, Dongyan; Xu, Zhihong; Li, Junkai; Qin, Zhaohai; Natural Product Research; (2019);,
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Related Products of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, methyl (2S)-5-amino-6-bromo-2-methyl-1,2,3,4-tetrahydroquinoline-1-carboxylate (300 mg, 1.00mmol, Intermediate 1) was dissolved in toluene (5 mL). Then 3,3- diethoxypropan-1-amine (885 mg, 6.01mmol), 3rd Generation BrettPhos precatalyst (91 mg, 0.10mmol), BrettPhos (108 mg, 0.20mmol) and sodium tert-butoxide (289 mg, 3.01mmol) were added successively. The resulting solution was stirred for 2 h at 110oC under nitrogen atmosphere. The reaction mixture was cooled and the resulting solids were filtered out. The filtrate was concentrated under vacuum. The residue was subjected to purification by FCC eluting with ethyl acetate/petroleum ether (2:1). This afforded the title compound (240 mg, 62%) as a yellow oil. MS: (ES, m/z): 366 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; SCHILLER, Shawn E.R.; HERBERTZ, Torsten; LI, Hongbin; GRAVES, Bradford; MISCHKE, Steven; WEST, Angela V.; ERICSSON, Anna; DOWNING, Jennifer R.; (484 pag.)WO2019/55877; (2019); A1;,
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Reference of 3401-47-6, A common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[Step 1] Synthesis of 1-(2-Fluorophenyl)-2-methoxynaphthalene Into a 500 mL three-neck flask were placed 8.7 g (35 mmol) of 1-bromo-2-methoxynaphthalene, and 5.0 g (35 mmol) of 2-fluorophenylboronic acid. The air in the flask was replaced with nitrogen. To this mixture were added 120 mL of toluene, 60 mL of ethanol, and 40 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80 C. for 8 hours under a nitrogen stream. The aqueous layer of the obtained mixture was subjected to extraction with toluene, and the obtained solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity-filtered. An oily substance obtained by concentration of the obtained filtrate was dissolved in about 30 mL of toluene. This solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the obtained filtrate was dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis was obtained in 60% yield. The reaction scheme of Step 1 is illustrated in (E2-1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US2012/165550; (2012); A1;,
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Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 645-36-3

2,2-Diethoxyethylamine (470 muL, 3.23 mmol) was added to a suspension of pyrimidine 9 (0.63 g, 2.67 mmol) in i-PrOH (30 mL), and the mixture was stirred at r.t. until the starting compound has dissolved. Et3N (560 muL, 4.0 mmol) was then added and the mixture was stirred for a further 45 min. H2O (50 mL) was added and the product was extracted with CH2Cl2 (2 × 50 mL). The organic layers were combined, washed with H2O (2 × 20 mL), dried (Na2SO4), and concentrated. The residue was purified by flash chromatography(silica gel, CH2Cl2; Rf = 0.42) to give a yellow solid; yield: 0.61 g(69%); mp 65.5-67.5 C.IR (KBr): 3380 (NH) cm-1. 1H NMR (300 MHz, CDCl3): delta = 1.27 (t, J = 6.9 Hz, 6 H, 2 × CH3),2.55 (s, 3 H, SCH3), 3.60 (dq, 2J = 9.3 Hz, 3J = 6.9 Hz, 2 H,2 × CHAHBCH3), 3.72-3.83 (m, 4 H, NCH2 and 2 × CHAHBCH3),4.09 (s, 3 H, OCH3), 4.68 (t, J = 5.4 Hz, 1 H, OCH), 8.84 (br s, 1 H,NH).13C NMR (75 MHz, CDCl3): delta = 14.8, 15.6, 44.3, 55.7, 63.2, 100.5,113.5, 156.6, 163.8, 174.6.Anal. Calcd for C12H20N4O5S: C, 43.36; H, 6.07. Found: C, 43.68;H, 6.11.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 645-36-3, its application will become more common.

Reference:
Article; Juskenas, Robertas; Masevicius, Viktoras; Tumkevicius, Sigitas; Synthesis; vol. 45; 17; (2013); p. 2438 – 2446;,
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Electric Literature of 450-88-4, These common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The solution of anisole of formula 2 (Scheme 6) (61 .5 g, 0.3 mol) in 1 ,2-dichloroethane (DCE) (600 mL) was cooled to -10 C and AICI3 was added in portions, maintaining the temperature below 2 C. The solution was then cooled to -5 C and acetyl chloride (56 mL, 0.79 mol) was added dropwise maintaining the internal temperature below 5 C. The reaction mixture was aged for 1 hour at 0 C. At this time HPLC showed no more starting material. The reaction mixture was quenched into ice (600 g) at a rate such that the internal temperature remained below 20 C. The resulting mixture was extracted with EtOAc (400 mL) and the organic phase then washed with 1 HCL (400 mL), saturated NaHC03 (400 mL) and brine (200 mL), dried over Na2S0 and filtered. The solvent was removed under reduced pressure to give acetophenon of formula 3 (Scheme 6) as a white solid (74.0 g, 100%): mp 1 13-1 17 C; H NMR (CDCI3) 5 2.59 (d, J = 5.1 Hz, 3H), 3.95 (s, 3H), 6.64 (d, J = 12.5 Hz, 1 H), 8.13 (d, J = 7.9 Hz, 1 H).

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
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Application of 116557-46-1,Some common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 3-bromo-2-methoxyaniline (3 g), 3-carboxyphenylboronic acid (2.94 g), bis(triphenylphosphine)palladium(II)chloride [PdCl2(PPh3)2] (0.30 g) and potassium carbonate (5.2 g) in ethanol (100 mL) and water (20 mL) was heated to about reflux temperature and stirred for about 28 hours. The hot mixture was filtered to remove the catalyst. The clear filtrate was concentrated under vacuum. To the residue, water (50 mL) and methanol (50 mL) was added, acidified to pH 3-5 using hydrochloric acid and stirred for about 30 minutes at about room temperature. The slurry was filtered, washed with n-hexane (50 mL) and dried in an oven at about 55 C. to about 60 C. for about 12 hours. Yield: 1.8 g 1H NMR (300 MHz in DMSO-d6): delta 8.08 (s, 1H), 7.89-7.92 (d, 1H), 7.73-7.75 (d, 1H), 7.51-7.56 (t, 1H), 6.87-6.92 (t, 1H), 6.72-6.74 (d, 1H), 6.50-6.53 (d, 1H), 3.27 (s, 3H)

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glenmark Generics Limited; Upadhye, Bhargav Krishnaji; Jagadale, Shivaji Eknath; Soni, Mukesh; US2015/87845; (2015); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene

Outside the glovebox, a 100 mL Schlenk flask equipped with a magnetic stir bar was charged with commercially available 3-(trifluoromethyl)benzoic acid (BFA) (3.09 g, 16.2 mmol) and bromoanisole BrMIP (3.60 g, 14.6 mmol). The flask was transferred to glovebox (%O2 ?0.005) and Pd(OAc)2 (157 mg, 5 mol %), n-butyl-di-1-adamantylphosphine (530 mg, 10 mol %), Cs2CO3 (11.92 g, 36.6 mmol) and powdered dry molecular sieves 3 A (1.0 g) were added. The flask was closed with the rubber septum and taken out of the glovebox. Anhydrous DMF degassed with nitrogen was added through the septum and the obtained mixture was first stirred at room temperature for 1 h under the positive pressure of nitrogen, and then placed in a preheated oil bath (145 C) for 24 h. The reaction mixture was cooled to room temperature and quenched with 2M HCl (100 mL). Ethylacetate (50 mL) was added and the resulting suspension was stirred for 15 min, filtered through a pad of celite and the layers were cut. The water layer was extracted with ethyl acetate (50 mL) and all organic phases were combined, washed with brine (50 mL) and evaporated under reduced pressure to obtain a yellow oil. The crude product was purified by column chromatography to give 4′-fluoro-5′-Isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carboxylic acid as a colorless oil (3.11g, 60%). 1H NMR (DMSO-d6) delta 0.95 (d, J = 8.0, 6H), 3.36 (s, 1H), 626 (d, J =12.0, 1H), 6.83 (d, J = 8.0, 1H), 7.03 (d, J = 8.0, 1H), 7.25 (m, 1H), 7.74 (s, 1H).

The synthetic route of 944317-92-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK Pharmaceuticals d.d.; EP2468736; (2012); A1;,
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