Analyzing the synthesis route of 891785-28-7

The synthetic route of 891785-28-7 has been constantly updated, and we look forward to future research findings.

891785-28-7, 6-Bromoisoquinolin-3-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

891785-28-7, [00344] 6-Bromo-3-fluoroisoquinoline: To a mixture of 6-bromoisoquinolin-3- amine (0.71 g, 3.18 mmol) in pyridine hydrofluoride (10 mL, 3.18 mmol) at -780C was carefully added sodium nitrite (0.26 g, 3.82 mmol). The reaction mixture was stirred at – 780C for 5 minutes. The reaction mixture was then warmed to room temperature over 40 minutes. The mixture was poured into an ice bath and the pH was adjusted to >9 with Na2CO3. The mixture was filtered to recover a yellow-purple solid. The solid was dissolved in EtOAc and water with stirring. The mixture was extracted with EtOAc (3 x 200 mL). The EtOAc was washed with brine, dried over Na2SO^ filtered and concentrated. The residue was taken up in DCM-MeOH and adsorbed onto silica gel. Purification by chromatography on silica gel eluting with EtOAc 0-7 % in hexanes provided the product (500 mg, 70 %). LCMS (API-ES) m/z: 226, 228 (M+H+).

The synthetic route of 891785-28-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMGEN INC.; WO2009/11880; (2009); A2;,
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Analyzing the synthesis route of 891785-28-7

The synthetic route of 891785-28-7 has been constantly updated, and we look forward to future research findings.

891785-28-7, 6-Bromoisoquinolin-3-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

891785-28-7, To a solution of 1,1′-thiocarbonyldipyridin-2(1H)one(0.251 g, 1.080 mmol) in dichloromethane at room temperature was added 6-bromoisoquinolin-3-amine (0.241 g, 1.080 mmol). The solution was stirred at room temperaturefor 3 hours. LC/MS indicated formation of the desired product.The deep orange solution was purified by silica gel chromatography (0-10% ethyl acetate-hexanes) to afford: 6-bromo-3-isothiocyanatoisoquinoline (0.1 g, 0.377 mmol,35% yield) as a yellow oil.

The synthetic route of 891785-28-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, JAMES H; MCDONALD, IVAR M; KING, DALTON; OLSON, RICHARD E; WANG, NENGHUI; IWUAGWU, CHRISTIANA I; ZUSI, F.CHRISTOPHER; MACOR, JOHN E; (330 pag.)JP5714745; (2015); B2;,
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Downstream synthetic route of 891785-28-7

As the paragraph descriping shows that 891785-28-7 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.891785-28-7,6-Bromoisoquinolin-3-amine,as a common compound, the synthetic route is as follows.

891785-28-7, 6-Bromo-3-fluoroisoquinoline. To a mixture of 6-bromoisoquinolin-3- amine (0.710 g, 3.18 mmol) in pyridine hydrofluoride (10 mL, 3.18 mmol) at -78C was carefully added sodium nitrite (0.26 g, 3.82 mmol). The reaction mixture was stirred at – 78C for 5 minutes. The reaction mixture was warmed to room temperature over 40 minutes. The mixture was poured into an ice bath, and the pH was adjusted to >9 with Na2COa. The mixture was filtered to recover a yellow-purple solid. The solid was dissolved in EtOAc – water with stirring. The mixture was extracted with EtOAc (3 x 200 mL). The EtOAc was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was taken up in DCM-MeOH and adsorbed onto silica gel. Purification by chromatography on silica gel (EtOAc 0-7 % in hexane) provided the product (500 mg, 70 %). LCMS (API-ES) m/z: 226, 228 (M+FT).

As the paragraph descriping shows that 891785-28-7 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; WO2009/11871; (2009); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

New learning discoveries about 891785-28-7

As the paragraph descriping shows that 891785-28-7 is playing an increasingly important role.

891785-28-7, 6-Bromoisoquinolin-3-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

891785-28-7, Steps 1-2 To a mixture of 6-bromoisoquinolin-3-amine (XX)(4.0 g, 17.93 mmol), Pd(dppf)Cl2-CH2Cl2 adduct (1.03 g, 1.26 mmol), KOAc (4.39 g, 44.83 mmol)and 4,4,5,5-tetramethyl-2-(4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (5.01 g, 19.72 mmol)in 1,4-dioxane (50 mL)was bubbled with N2 for 2 min. The reaction mixture was sealed and heated at 90 C. for 1.5 h. The reaction was cooled to room temperature, filtered and washed with EtOAc. The filtrate was concentrated and the residue taken in dioxane (50 mL). To the suspension was added 4-bromo-2-methyl-pyrazole-3-carbaldehyde (XLVIII)(3.39 g, 17.93 mmol)followed by K3PO4 (9.52 g, 44.83 mmol), Pd(dppf)Cl2-CH2C2 adduct (1.03 g, 1.26 mmol)and water (15 mL). The mixture was purged with N2 for a min, sealed and heated again at 90 C. for 19 h. The mixture was cooled to room temperature and concentrated to about 20 mL. The concentrate was diluted with EtOAc and filtered through a pad of Celite. The filtrate was diluted with water and the organic layer separated. The organic layer was washed with brine; dried, filtered and concentrated. The residue was triturated in ether and the resulting solid filtered to afford 4-(3-amino-6-isoquinolyl)-2-methyl-pyrazole-3-carbaldehyde (XLIX)(4.1 g, 16.2 mmol, 90.6% yield)as a brown solid. 1H NMR (499 MHz, DMSO-d6)delta ppm 0.01 (6H, s), 0.86 (9H, s), 0.88-1.00 (2H, m), 1.23-1.35 (2H, m), 1.35-1.46 (1H, m), 1.69-1.79 (2H, m), 1.85-1.95 (2H, m), 2.21 (1H, tt, J=12.21, 3.57 Hz), 3.38 (2H, d, J=6.31 Hz), 3.57 (3H, s)ESIMS found for C14H12N4O m/z 252.95 (M+1).

As the paragraph descriping shows that 891785-28-7 is playing an increasingly important role.

Reference£º
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Eastman, Brian Walter; Cao, Jianguo; Bollu, Venkataiah; Mittapalli, Gopi Kumar; Chiruta, Chandramouli; (218 pag.)US2017/313682; (2017); A1;,
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Downstream synthetic route of 891785-28-7

As the paragraph descriping shows that 891785-28-7 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.891785-28-7,6-Bromoisoquinolin-3-amine,as a common compound, the synthetic route is as follows.

891785-28-7, A mixture of 6-bromoisoquinolin-3-amine (XV) (2.57 g, 11.52 mmol), 1-methyl-5-(tributylstannyl)-1H-imidazole (LXXI) (Combi-blocks) (4.28 g, 11.53 mmol), Pd(PPh3)4 (1.39 g, 1.2 mmol) in dioxane (57.6 mL) was purged with N2 gas for 10 min and then heated to 90 C. overnight. The solvent was evaporated under high vacuum and the residue was purified by column chromatography (0?10% MeOH/CHCl3) to give 6-(3-methylimidazol-4-yl)isoquinolin-3-amine (LXXII) as an olive green solid (2.32 g, 9.83 mmol, 85.3% yield). ESIMS found for C13H12N4 m/z 225.1 (M+H).

As the paragraph descriping shows that 891785-28-7 is playing an increasingly important role.

Reference£º
Patent; Samumed, LLC; KC, Sunil Kumar; Mittapalli, Gopi Kumar; Chiruta, Chandramouli; Hofilena, Brian Joseph; Mak, Chi Ching; Eastman, Brian Walter; Bollu, Venkataiah; (158 pag.)US2019/119263; (2019); A1;,
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Simple exploration of 891785-28-7

891785-28-7 6-Bromoisoquinolin-3-amine 45789831, aisoquinoline compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.891785-28-7,6-Bromoisoquinolin-3-amine,as a common compound, the synthetic route is as follows.

891785-28-7, To a suspension of 6-bromoisoquinolin-3-amine (XV) (10 g, 44.83 mmol) and 2-chloroacetic anhydride (L) (9.2 g, 53.79 mmol) in dry THF (100 mL) was added TEA (15.62 mL, 112.07 mmol). The mixture was stirred at room temperature for 16 h then poured into a mixture of aqueous saturated NaHCO3 (200 mL) and water (300 mL). The mixture was stirred for an hour and the resulting solids were collected by filtration, air-dried and suspended in diethyl ether (400 mL), stirred for 30 min. The solid filtered and dried under high vacuo to obtain N-(6-bromoisoquinolin-3-yl)-2-chloroacetamide (LI) as a brown solid (9.36 g, 31.25 mmol, 69.7% yield). ESIMS found for C11H8BrClN2O m/z 298.95 (M+1).

891785-28-7 6-Bromoisoquinolin-3-amine 45789831, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Eastman, Brian Walter; Cao, Jianguo; Mittapalli, Gopi Kumar; (82 pag.)US2019/125741; (2019); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Simple exploration of 891785-28-7

891785-28-7 6-Bromoisoquinolin-3-amine 45789831, aisoquinoline compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.891785-28-7,6-Bromoisoquinolin-3-amine,as a common compound, the synthetic route is as follows.

891785-28-7, 6-Bromo-3-fluoroisoquinoline: To a mixture of 6-bromoisoquinolin-3- amine (0.710 g, 3.18 mmol) in pyridine hydrofluoride (10.0 mL, 3.18 mmol, Aldrich) at – 78 0C was carefully added sodium nitrite (0.264 g, 3.82 mmol, Aldrich). The reaction mixture was stirred at -78 0C for 5 minutes. The reaction mixture was then warmed to room temperature and stirred for 40 minutes. The mixture was then poured into an ice bath and the pH was adjusted to >;9 with Na2CO3. The mixture was filtered to recover a yellow-purple solid. The solid was dissolved in EtO Ac-water with stirring. The resulting mixture was then extracted with EtOAc (3 x 200 mL). The EtOAc layers were combined, washed with brine, dried over Na2SOzI, filtered and concentrated. The residue was taken up in DCM-MeOH and adsorbed onto silica gel. Purification by chromatography on silica gel (eluting with EtOAc O – 7 % in hexanes) provided 6-bromo- 3-fluoroisoquinoline (500 mg, 70 %). LCMS (API-ES) m/z: 226.0, 228.0 [M+H]+.

891785-28-7 6-Bromoisoquinolin-3-amine 45789831, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; AMGEN INC.; ZENG, Qingping; YUAN, Chester Chenguang; YAO, Guomin; WANG, Xianghong; TADESSE, Seifu; ST. JEAN, JR., David J.; REICHELT, Andreas; LIU, Qingyian; HONG, Fang-Tsao; HAN, Nianhe; FOTSCH, Christopher H.; DAVIS, Carl D.; BOURBEAU, Matthew P.; ASHTON, Kate S.; ALLEN, John G.; WO2010/83246; (2010); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Some tips on 891785-28-7

891785-28-7 6-Bromoisoquinolin-3-amine 45789831, aisoquinoline compound, is more and more widely used in various.

891785-28-7, 6-Bromoisoquinolin-3-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

891785-28-7, To a stirred suspension of 6-bromoisoquinolin-3-amine (XV) (2.0 g, 8.97 mmol) and DMAP (0.22 g, 1.79 mmol) in pyridine (30 mL) was added cyclopropanecarbonyl chloride (LXV) (0.98 mL, 10.76 mmol) and the mixture was stirred at room temperature for 2 h. Another 0.5 equivalents of cyclopropanecarbonyl chloride was added and stirring continued at room temperature for another 1 h. The reaction went to completion, solvent was concentrated and the residue taken up in EtOAc and washed with water. The organic/aqueous layer was filtered, washed with EtOAc and the solids were dried under high vacuo to obtain 440 mg of the product. The filtrates were transferred to separating funnel, organic layer separated, washed with brine solution, dried over anhydrous Na2SO4 and then concentrated to dryness to obtain N-(6-bromo-3-isoquinolyl)cyclopropanecarboxamide (LXVI) as a brown solid (1.74 g, 5.98 mmol, 66.7% yield). ESIMS found for C13H1lBrN2O m/z 291.0 (M+H).

891785-28-7 6-Bromoisoquinolin-3-amine 45789831, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Hofilena, Brian Joseph; Mittapalli, Gopi Kumar; Eastman, Brian Walter; Cao, Jianguo; Bollu, Venkataiah; Chiruta, Chandramouli; (149 pag.)US2019/125740; (2019); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

New learning discoveries about 891785-28-7

As the paragraph descriping shows that 891785-28-7 is playing an increasingly important role.

891785-28-7, 6-Bromoisoquinolin-3-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3 A mixture of DIPEA (5.86 mL, 33.62 mmol), DMAP (0.27 g, 2.24 mmol) and HATU (5.11 g, 13.45 mmol) in DMF (30 mL) was stirred for 10 min. 6-Bromoisoquinolin-3-amine (XII) (2.5 g, 11.21 mmol) was then added followed by the addition of trans-4-[[tert-butyl (dimethyl)silyl]oxymethyl]cyclohexanecarboxylic acid (LIII) (3.66 g, 13.45 mmol). The mixture was heated to 70 C. overnight. An additional 0.5 equiv. of HATU were added and the mixture was continued for additional 6 h. The solvent was concentrated, the residue taken up in EtOAc, washed with sat. NaHCO3 and brine. The organic layer was then concentrated and the crude product was purified by column chromatography (0?30% EtOAc/hexanes). The pure fractions were combine and concentrated to obtain trans-N-(6-bromo-3-isoquinolyl)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclohexanecarboxamide (LIV) (2.25 g, 4.71 mmol, 42.0% yield) as a crystalline off-white solid. 1H NMR (499 MHz, DMSO-d6) delta ppm 0.03 (6H, s), 0.87 (9H, s), 0.98 (2H, qd, J=12.72, 3.29 Hz), 1.38-1.51 (3H, m), 1.73-1.82 (2H, m), 1.85-1.92 (2H, m), 2.46-2.55 (1H, m), 3.41 (2H, d, J=6.04 Hz), 7.62 (1H, dd, J=8.64, 1.78 Hz), 7.99 (1H, d, J=8.78 Hz), 8.16 (1H, d, J=1.65 Hz), 8.44 (1H, s), 9.13 (1H, s), 10.53 (1H, s); ESIMS found for C23H33BrN2O2Si m/z 477.2 (79BrM+1).

As the paragraph descriping shows that 891785-28-7 is playing an increasingly important role.

Reference£º
Patent; Samumed, LLC; KC, Sunil Kumar; Mittapalli, Gopi Kumar; Hofilena, Brian Joseph; Marakovits, Joseph Timothy; Chiruta, Chandramouli; Mak, Chi Ching; Cao, Jianguo; (324 pag.)US2017/313681; (2017); A1;,
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