Month: June 2021

Synthetic Route of 7664-66-6, 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. 7664-66-6, name is 4-Isopropoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[Example 45] Preparation of 1-(4-chlorobenzyl)-2-(4-isopropoxyphenylimino)-dihydro-pyrimidine-4,6-dion (I-322) To a mixture of 4-isopropoxyaniline (15 g, 99 mmol) and acetonitrile (150 mL) was added gradually benzoylisothiocyanate (13.4 mL, 99 mmol) under ice-cooling, and the resulting mixture was stirred at room temperature for 50 minutes. To the reaction mixture were added gradually 4-chlorobenzylamine (12.1 mL, 99 mmol), triethylamine (13.8 mL, 99 mmol), and 1-ethyl-3-(3-dimethyl-aminopropyl) carbodiimide hydrochloride (20.9 g, 109 mmol) under ice-cooling, and the resulting mixture was stirred at room temperature for 2.5 hours. To the reaction mixture was added water (200 mL), and the mixture was extracted with toluene (300 mL). The extract was washed by brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resulting residue was precipitated by toluene and hexane to give N-((4-chlorobenzylamino)(4-isopropoxyanilino)methylene)benzamide (38.1 g, Yield: 91%) as white powder. 1H-NMR (delta ppm TMS/CDCl3): 1.34 (6H, d, J=6.0 Hz), 4.52 (1H, sept, J=6.0 Hz), 4.72 (2H, d, J=6.2 Hz), 5.09 (1H, brs), 6.87-6.92 (2H, m), 7.13-7.18 (2H, m), 7.24-7.31 (4H, m), 7.36-7.48 (3H, m), 8.21-8.25 (2H, m), 11.9 (1H, brs).

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

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2734-70-5, name is 2,6-Dimethoxyaniline, 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 2734-70-5, Recommanded Product: 2,6-Dimethoxyaniline

General procedure: To a solution of aniline (0.93 g,10 mmol) in 10% HCl (50 mL) cooled in an ice-bath was added NaNO2 (0.74 g,10.7 mmol). The mixture was stirred at 0 C for 0.5 h and followed by the addition of NaN3 (0.72 g,11 mmol). The mixture was stirred at 0 C for 0.5 h and the aqueous layer was extracted by EtOAc (3×50 mL). The organic layer was dried over MgSO4 overnight. After filtration, EtOAc was evaporated to give 20a as yellow oil (1.09 g, yield 92%), which was used directly in the next reaction without further purification. Compounds 20b-20z and 20aa were prepared from compounds19b-19z and 19aa in a similar manner as described for compound 20a, respectively.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,6-Dimethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cao, Jiangying; Zang, Jie; Kong, Xiujie; Zhao, Chunlong; Chen, Ting; Ran, Yingying; Dong, Hang; Xu, Wenfang; Zhang, Yingjie; Bioorganic and Medicinal Chemistry; vol. 27; 6; (2019); p. 978 – 990;,
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Adding a certain compound to certain chemical reactions, such as: 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, 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 929-75-9, Formula: C8H20N2O3

To 4-carboxymethyl-7-[1-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-1H-1,2,3-triazol-4-yl]-2H-chromen-2-one (7a, 200 mg, 0.273 mmol) and 1,11-diamino-3,6,9-trioxaundecane (8c, 53 mg, 0.273 mmol) in THF (10 mL) at room temperature was added benzotriazole-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (121 mg, 0.273 mmol), and the mixture was stirred at the same temperature for 1 h. The solvent was removed, and the resulting slurry was diluted with saturated aqueous NaHCO3 and extracted with methylene chloride several times. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on a silica gel column with methylene chloride and MeOH (7:1) to give the desired product 10e (113 mg, 46%). Mp 303.9+/-0.7 C; 1H NMR (500 MHz, DMF-d7): delta=8.92 (s, 1H), 8.44 (br t, J=5.6 Hz, 1H), 7.99 (d, J=8.3 Hz, 1H), 7.94 (dd, J=8.3 and 1.5 Hz, 1H), 7.89 (d, J=1.5 Hz, 1H), 6.52 (s, 1H), 4.74 (t, J=7.0 Hz, 2H), 3.92 (s, 2H), 3.78 (m, 2H), 3.63-3.67(m, 2H), 3.60-3.63 (m, 2H), 3.57-3.60 (m, 4H), 3.55 (t, J=5.6 Hz, 2H), 3.40 (q, J=5.6 Hz, 2H), 3.24-3.33 (m, 2H), 2.43-2.56 (m, 2H), 2.31-2.31 ppm (m, 2H); 13C NMR (125 MHz, DMF-d7): delta=168.4, 160.2, 154.4, 151.1, 145.7, 135.0, 126.6, 123.2, 121.3, 119.1, 116.0, 112.9, 70.35, 70.27, 70.21, 70.18, 69.5, 67.2, 49.1, 40.1, 39.94, 39.91, 39.7, 39.6, 39.5, 39.4, 39.2, 27.8 (t, J=19.2 Hz), 21.6 ppm (t, J=3.5 Hz); IR (ATR, neat): nu=2925, 1719 (CO), 1654 (CO), 1622, 1238, 1203, 1147, 1056, 1027, 1009, 1004, 832, 823, 763 cm-1; MS (ESI): m/z: 906 [M+H+]; HRMS (EI): m/z calcd for C32H32F17N5O6: 905.2081 [M+]; [M+] not found.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,11-Diamino-3,6,9-trioxaundecane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jeon, Moon-Kook; Kang, Myoung-Ku; Park, Koon Ha; Tetrahedron; vol. 68; 30; (2012); p. 6038 – 6053;,
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Synthetic Route of 74654-07-2, These common heterocyclic compound, 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, 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.

A solution of cyanoacetic acid (621 mg, 7.3 mmol) in anhydrous DCM (15 mL) was cooled to 0 C. Separately, a solution of hydroxybenzothiazole (HOBt) (1.48 g, 10.97 mmol) and 2-(2-(2-methoxyethoxy)ethoxy)ethanamine (A2, 1.79 g, 10.97 mmol) was prepared in DCM (10 mL); this solution was then added dropwise to the cooled solution of cyanoacetic acid. The resulting solution was allowed to stir for 10 minutes at 0 C., upon which 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (2.1 g, 10.97 mmol) was added in one portion and the reaction stirred under argon at 0 C. for 12 hours. The reaction was then concentrated and purified by silica gel chromatography (0-2% MeOH/DCM) to obtain 2-cyano-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)acetamide A3 as a yellow oil in 83% yield.

Statistics shows that 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine is playing an increasingly important role. we look forward to future research findings about 74654-07-2.

Reference:
Patent; The Regents of the University of California; Amydis, Inc.; Yang, Jerry; Theodorakis, Emmanuel A.; Sarraf, Stella; US2018/327373; (2018); A1;,
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Related Products of 59557-91-4, 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. 59557-91-4, name is 4-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

STEP 2: tert-Butyl 7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2,3- dihydrobenzoxazepine-4(5H)-carboxylate (500 mg, 2.33 mmol), 4-bromo-2- methoxyaniline (296 mg, 1.47 mmol), potassium carbonate (737 mg, 5.34 mmol) and [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (97.5 mg, 0.13 mmol) were heated at HO0C in DME (7 mL) and water (1 mL) over 48 h. The mixture was then cooled to room temperature and diluted with an excess of ethyl acetate and filtered through a bed of celite. The filtrate was partitioned with water and the organic phase washed with brine and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated and the residue purified by silica chromatography using 85:15 hexanes: ethyl acetate as eluent to give 1,1-dimethylethyl 7-[4-amino-3- (methyloxy)phenyl]-2,3-dihydro-l,4-benzoxazepine-4(5H)-carboxylate (198 mg, 40%). MS (EI) C2IH26N2O4: 371 (MH+).

The synthetic route of 4-Bromo-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; ANAND, Neel, Kumar; BAIK, Tae-Gon; BLAZEY, Charles, M.; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen; JOSHI, Anagha; KIM, Angie, Inyoung; MANALO, Jean-Claire, Limun; PETO, Csaba, J.; RICE, Kenneth, D.; TSANG, Tsze, H.; WO2010/135568; (2010); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., Recommanded Product: 6298-96-0

A mixture of (S)-1-(4-methoxyphenyl)-ethylamine (475 mg) and 6-chloropurine riboside (300 mg) in PrOH (70 ml) was heated to 70C and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over Sephadex LH-20 gel and eluted with ethanol to yield N6-[(S)-1-(4-methoxyphenyl)-ethyl]-adenosine(345 mg) as a white solid: positive ESIMS m/z 402 [M + H]+ and 424 [M + Na]+; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.38 (1H, s, H-2), 8.23 (1H, brs, -NH), 8.18 (1H, s, H-8), 5.90 (1H, d, J= 6.3 Hz, H-1′), 5.46 (1H, d, J= 6.3 Hz, -OH), 5.42 (1H, m, -OH), 5.20 (1H, d, J= 4.5 Hz, -OH), 4.61 (1H, m, H-2′), 4.16 (1H, m, H-3′), 3.98 (1H, m, H-4′), 3.66 (1H, m, H-5’a), 3.54 (1H, m, H-5’b); the (S)-1-(4-methoxyphenyl)-ethyl moiety delta 7.35 (1H, d, J = 8.4 Hz, H-2′, H-6′), 6.84 (1H, d, J = 8.4 Hz, H-3′, H-5′), 5.48 (1H, m, H-7′), 3.71 (3H, s, -OCH3), 1.51 (3H, d, 7.2Hz, H-8′); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety delta,153.9 (s, C-6), 152.3 (d, C-2), 148.6 (s, C-4), 139.8 (d, C-8), 119.7 (s, C-5), 88.0 (d, C-1′), 85.9 (d, C-4′), 73.6 (d, C-2′), 70.7 (d, C-3′), 61.7 (t, C-5′); the (S)-1-(4-methoxyphenyl)-ethyl moiety delta 158.0 (s, C-4′), 137.1 (s, C-1′), 127.3 (d, C-2′, C-6′), 113.6 (d, C-3′, C-5′), 55.0 (q, -OCH3), 48.2 (d, C-7′), 22.5 (q, C-8′)o

The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF MEDICAL SCIENCES; EP2511283; (2012); A1;,
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These common heterocyclic compound, 41406-00-2, name is 3-Isopropoxyaniline, 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. Formula: C9H13NO

EXAMPLE A; 3-(3-Isopropoxy-phenyl)-2-thioxo-2,3-dhydr-1H-quinazolin-4-one To a solution of 3-isopropoxy aniline (6.0 g, 40 mmol) in 150 ml of CHCl3 was added dropwise thiophos-gene (2.81 ml, 44 mmol) at 0 C. After the addition of thiophosgene, triethylamine (7.0 ml, 48 mmol) was added slowly and the reaction mixture was stirred for 2 hours at room temperature. It was then concentrated and diluted with 200 ml of ethyl acetate. The triethylamine hydrochloride salt was filtered off and the filtrate was concentrated to yield crude 3-isopropoxyphenyl isothiocyanate.The crude 3-isopropoxyphenyl isothiocyanate was dissolved in 150 ml of acetic acid, and anthranilic acid (6.04 g, 44 mmol) was added. The resulting reaction mixture was refluxed for 16 hours and then cooled to room temperature. The white solid was separated which was filtered to yield 9.0 g of the title compound (72.1%) mp 288-290 C.

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

Reference:
Patent; Warner-Lambert Company; US6897213; (2005); B1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, A new synthetic method of this compound is introduced below., Formula: C4H8Br2O

To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2,4 mmol) in one portion. The mixture was stirred at 25C for 5 min before 2- bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred further at 25C for 5 h and at 75 0C for 72 h before it was cooled to 25C} quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO45 filtered and concentrated. Purification of the residue on silica gel elutmg with 0% to 70% ethyl acetate/hexanes afforded Cap- 143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond. MS-Wl); 90% homogenily index; LCMS: Anal. CaIc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LOPEZ, Omar D.; CHEN, Qi; BELEMA, Makonen; WO2010/138368; (2010); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 910251-11-5, name is Potassium trifluoro(methoxymethyl)borate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C2H5BF3KO

Intermediate 52a 6-chloro-3-(methoxymethyI)-l-trityl-lH-pyrazolo[43-c]pyridine Under Argon, the solution of 6-cUoro-3-iodo-l-trityl-lH-pyrazolot4,3-c]pyridine (52 mg, 0.100 mmol), potassium methoxymethyltrifluoroborate (16.66 mg, 0.110 mmol), palladium(n) acetate (0.671 mg, 2.99 mupiiotaomicron), (2-DICYCLOHEXYLPHOSPfflNO-2′,6′- DIISOPROPYL-l,l’-BIPHENYL)[2-(2-AMINOETHYL)PHENYL)]PALLADIUM(n) (4.36 mg, 5.98 mol) and cesium carbonate (0.024 ml, 0.299 mmol) in 1,4-Dioxane (0.9 ml) and Water (0.1 ml) was allowed to stir at 100 C for 24h. LC-MS showed the desired product’s mass. EtOAc was added into the mixture and the organic layer was washed by water and brine. After drying over Na2S04 the organic layer was evaporated under reduced pressure yielding 6- c oro-3-(memoxymethyl)-l-1rityl-lH-pyrazolo[4,3-c]pyridine, 52a. The intermediate was taken to the next reaction without further purification. MS ESI Calc’d for C27H22CIN3O [M+H]+ 440, found 440.

According to the analysis of related databases, 910251-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; KELLEY, Elizabeth Helen; METHOT, Joey, L.; ZHOU, Hua; PETROCCHI, Alessia; MANSOOR, Umar Faruk; FISCHER, Christian; O’BOYLE, Brendan, M.; GUERIN, David Joseph; BIENSTOCK, Corey, E.; BOYCE, Christopher, W.; DANIELS, Matthew, H.; FALCONE, Danielle; FERGUSON, Ronald, D., II; FEVRIER, Salem; HUANG, Xianhai; LIPFORD, Kathryn Ann; SLOMAN, David, L.; WILSON, Kevin; ZHOU, Wei; WITTER, David; MALETIC, Milana, M.; SILIPHAIVANH, Phieng; WO2013/63214; (2013); A1;,
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Synthetic Route of 104197-14-0, 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. 104197-14-0, name is 4-Bromo-2,6-difluoroanisole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example A5; 4-(3,5-Difluoro-4-(l-(4-(trifluoromethyl)benzyl)azetidin-3-yloxy)phenyl)-l-(methylsulfonyl)piperidineineA5g Example A5[0022] Step A: In a microwave vial, a mixture of pyridin-4-ylboronic acid (160 mg, 1.3 mmol), 5-bromo-l,3-difluoro-2-methoxybenzene A5a (223 mg, 1 mmol) and Pd(PPh3)4 (58 mg, 0.05 mmol) is dissolved/suspended in dimethylformamide (3 mL). To the mixture are added cesium carbonate (978 mg, 3 mmol) and water (3 mL). The vial is sealed and subjected to microwave irradiation (150 C, 15 min). The mixture is filtered through a syringe filter and washed with ethyl acetate. Water is added and the mixture extracted with ethyl acetate (4x). The organic phase is dried over sodium sulfate and concentrated. The crude material is purified by flash chromatography (ethylacetate/hexanes gradient) to afford 4-(3,5-difluoro-4-methoxyphenyl)pyridine A5b as a white solid: 1H-NMR (400 MHz, CDC13) delta 8.69 (d, J= 6 Hz, 2 H), 7.44 (d, J= 6 Hz, 2H), 7.22 (d, J = 9.6 Hz, 2H), 4.09 (s, 3H); MS calcd. for C12Hi0F2NO ([M+H]+): 222.1, found: 222.1.

The synthetic route of 4-Bromo-2,6-difluoroanisole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; AZIMIOARA, Mihai; COW, Christopher; EPPLE, Robert; LELAIS, Gerald; MECOM, John; NIKULIN, Victor; WO2011/44001; (2011); A1;,
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