Month: October 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23687-25-4,Isoquinolin-4-amine,as a common compound, the synthetic route is as follows.

Example 17 N-(1-Methyl-5-indolyl)-N’-(4-isoquinolyl) urea (E17) The title compound was prepared from 4-aminoisoquinoline, 1,1′-carbonyl diimidazole and 5-amino-1-methyl-indole using a procedure similar to that described for Example 1, and then converted to the hydrochloride salt using hydrogen chloride in ether/ethanol, in 26% overall yield, m.p. 195-197 C., 23687-25-4

The synthetic route of 23687-25-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SmithKline Beecham, p.l.c.; US5508288; (1996); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

58142-99-7,58142-99-7, 5-Iodoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Tert-butyl (R)-2-methyl-5-carbonylpiperazine-1-carboxylate (1.1 g, 5.14 mmol),5-Iodoisoquinoline(1.64 g, 6.43 mmol), cuprous iodide (356 mg, 1.87 mmol), potassium phosphate (3.34 g, 9.87 mmol), ethylenediamine (3 mL), 4A molecular sieves (10 g) dissolved in 1,4- Dioxane (50 mL) reacts overnight at 120C in a nitrogen atmosphere.The reaction was monitored by LCMS, followed by filtration with water. The filtrate was extracted with dichloromethane three times. The organic phases were combined, dried, and the solvent was removed by rotary evaporation. Column chromatography gave 4-isoquinoline-(R)-2-methyl-5-carbonyl. Tert-butyl piperazine-1-carboxylate (537 mg, yield: 31%).

58142-99-7 5-Iodoisoquinoline 11391181, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Gang; Wu Yongyong; Yu Hua; Wang Kunjian; Li Xiaoyong; Sun Ling; Wang Runjiang; Chen Qiangqiang; Yang Long; Song Hongmei; Zeng Hong; Zhang Hong; Ye Qijun; Wang Lichun; Wang Jingyi; (98 pag.)CN107540659; (2018); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1532-97-4,4-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

Reference Example 1 4-Fluoroisoquinoline A solution of n-butyllithium in n-hexane (1.58 M, 60.1 ml, Kanto Chemicals) was added with tetrahydrofuran (345 ml), and the mixture was sufficiently cooled on a dry ice-acetone bath. The mixture was added dropwise with a solution of 4-bromoisoquinoline (9.0 g, Tokyo Kasei Kogyo) in tetrahydrofuran (65 ml) over 1 hour so that the temperature of the reaction mixture should not exceed -65¡ã C. The mixture was stirred at the same temperature for 30 minutes, and then added dropwise with a solution of N-fluorobenzenesulfonimide (30 g, Tokyo Kasei Kogyo) in tetrahydrofuran (100 ml) over 1 hour so that the temperature of the reaction mixture should not exceed -65¡ã C. Subsequently, the mixture was stirred at the same temperature for 1 hour, then the cooling bath was removed, and the mixture was gradually warmed to room temperature. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate (300 ml) and ethyl acetate (300 ml), and stirred at room temperature for 12 hours. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate 3 times (200 ml for each time). The combined organic layer was washed with saturated brine (500 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was added with chloroform (250 ml), and the insoluble matters were removed by filtration. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5:1) to obtain the title compound (3.6 g). MS (m/z): 148 (MH+) 1H-NMR (CDCl3) delta (ppm): 7.26-7.71 (1H, m), 7.75-7.82 (1H, m), 8.03 (1H, dd, J=1.2 Hz, J=8.4 Hz), 8.10 (1H, d, J=8.4 Hz), 8.38 (1H, s), 9.08 (1H, s)

1532-97-4, 1532-97-4 4-Bromoisoquinoline 73743, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Asahi Kasei Pharma Corporation; US2007/179127; (2007); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23687-26-5,6-Aminoisoquinoline,as a common compound, the synthetic route is as follows.

A mixture of 2 (340.41 g assay-corrected, 1.0 equiv.), collidine (1.3 equiv.) and 6-aminoisoquinoline (1.3 equiv.) in DMF at 0¡ã C. in a 50 L reactor was treated rapidly with a solution of 2,2,2-trichloro-1 , 1 -dimethylethyl chloroformate (1.3 equiv.) in DMF in a single portion. The reaction was exothermic, with a rise in temperature to about 10¡ã C. Upon stirring for a minimum of 60 minutes, the reaction was assayed by TLC and deemed complete when two samples taken one hour apart showed no further conversion. Thereaction was quenched by the addition of 10percent KHCO3 (aq.), followed by diluting with ethyl acetate, washing with citric acid, a final 10percent KHCO3 (aq.) wash and concentrating to near dryness to afford a crude residue.The crude residue was dissolved in dichloromethane/ethylacetate (1:1) and the resulting solution returned to the 50 Lreactor, where it was stirred for 4.5 h. The resulting solution was filtered through a 10 jim Teflon filter to remove a colloidal solid. The selection of a 10 jim Teflon filter was based on the filter having enough surface area and beingchemically compatible with the dichloromethane/ethyl acetate (1:1) solvent mixture. Concentration of the filtrate in vacuo yielded 666.3 g of crude material.The resulting crude product was diluted with dichloromethane to give a solution that was divided into two portions for silica gel chromatography. The splitting of the dichloromethane solution maintained a 25:1 ratio of silicagel to crude product found to be useful for successful 41Fractions containing a high concentration of the desired material, irrespective of the impurities content, were combined and concentrated to afford 363.3 g of an off-white solid.The off-white solid was dissolved in dichloromethane and filtered through a 10 tm Teflon filter. The bulk of the solvent was then distilled off and the remainder gradually switched to acetonitrile via chase distillation. At this point, a white solid crystallized and the mixture was cooled to 0¡À5¡ã C. Thesolid was isolated by filtration and dried to obtain 333.7 g ofa white solid. A sample of the solid was subjected to TLCand HPLC purity analyses. No impurities could be detected by TLC, but the HPLC analysis showed the presence of an unspecified impurity at a level of 0.4 6percent while all identified impurities were below In-Process Action Levels.A first recrystallization from dichloromethane/heptane was then implemented. Afier dissolving the solid in dichloromethane, heptane was added and the resulting mixture stirred for 4 hat room temperature. A white solid crystallized out. The solid was filtered and dried to obtain 307.0 g of the solid. A sample of the solid was taken and subjected to TLC and HPLC purity analyses. No impurities could be detected by TLC, but the HPLC analysis showed the presence of the same unspecified impurity, but was reduced to a level of0.28percent.2025purification. The two portions of dichloromethane solution represented 166.5 g and 170.2 g of the crude product respectively. The purifications were achieved through theuse of two 5 kg silica gel colunms eluting with ethyl acetate/heptane (60:40) until the desired product had eluted.white solid was filtered and dried to obtain the title compound as a white solid (272.1 g; 60.5percent assay-correctedA fourth recrystallization from dichloromethane/heptane was utilized. After dissolving the solid in dichloromethane, heptane was added and the resulting mixture stirred for 4 h at room temperature during which time a white solid crystallized out. The white solid was filtered, dried, and sub-jected to HPLC purity testing. The impurity was detected at less than 0.05percent. The fourth recrystallization from dichloromethane/heptane yielded 250.9 g (55.3percent assay corrected yield) of the title compound as a white solid.To achieve even higher purities of the desired product, it may be useful to implement additional recrystallizations. ?H NMR (500 MHz, d5-DMSO) oe 1.32 (s, 9H), 2.29 (s, 3H), 2.49 (s, 3H), 3.3 (m, 1H), 3.56 (m, 1H), 4.11 (m, 1H), 5.25 (s, 2H), 7.02 (bt, J=5.4 Hz, 1H), 7.07 (d, J=8.4H, 1H), 7.11(s, 1H), 7.43 (s, 4H), 7.68 (m, 2H), 7.75 (d, J=7.9 Hz, 1H),8.02 (d, J=8.7 Hz, 1H), 8.38 (s, 1H), 8.39 (d, J=5.7 Hz, 1H),9.14 (s, 1H). 13C NMR (125 MHz, d5-DMSO) oe 20.8, 21.2,28.2, 42.9, 51.7, 65.6, 77.8, 113.1, 120.0, 121.0, 125.0,126.1, 126.6, 128.0, 128.1, 128.5, 130.4, 132.3, 135.2,136.1, 137.8, 139.5, 140.4, 142.4, 143.2, 151.5, 155.8,166.4, 171.0. LC-MS (ES+): mlz=554 (M+1), 576 (M+23).yield).

23687-26-5, As the paragraph descriping shows that 23687-26-5 is playing an increasingly important role.

Reference£º
Patent; Aerie Pharmaceuticals, Inc.; Sturdivant, Jill M.; deLong, Mitchell A.; Chambournier, Gilles; Pamment, Michael G.; Fedij, Victor; (31 pag.)US9643927; (2017); B1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

164148-92-9, tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of 3-bromo-2-methylbiphenyl (Example 2, Step 1: 30 mg, 0.1 mmol), palladium acetate (2.7 mg, 0.012 mmol), (R)-(+)-2,2?-bis(diphenylphosphino)-1,1?-binaphthyl (7.6 mg, 0.012 mmol), and cesium carbonate (120 mg, 0.37 mmol) in 1,4-dioxane was added tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (Oakwood cat011348: 33 mg, 0.13 mmol) under N2. The reaction mixture was stirred at 120 C. overnight. The crude reaction mixture was cooled to room temperature, diluted with ethyl acetate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-20%) to afford the desired product. LC-MS calculated for C27H31N2O2 (M+H)+: m/z 415.2; found: 415.2.

164148-92-9, The synthetic route of 164148-92-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.,18881-17-9

Step 2: Compound A2 (5.3 g, 16.47 mmol) and (S)-(1,2,3,4-tetrahydroisoquinolin-3- yl)methanol (2.96 g, 18.12 mmol) were dissolved in DCM (47.1 mL). The reaction mixture was cooled to 0 C and TEA (3.44 mL, 24.71 mmol) was added dropwise under Ar. The reaction mixture was then warmed to rt and was stirred overnight. The solution was concentrated and the crude product was purified by silica gel chromatography (EtOAc/hexanes, gradient, 0% to 80%) to obtain compound A3 (7.22 g, 16.10 mmol, 98% yield). LCMS = 5.482 mm (8 mm method). Mass observed (ESI): 449.25 (M+H).

18881-17-9 (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol 776757, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; IMMUNOGEN, INC.; MILLER, Michael, Louis; SHIZUKA, Manami; CHARI, Ravi, V.J.; (312 pag.)WO2019/133652; (2019); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

23687-26-5, 6-Aminoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To (S)-3-[(tert-butoxycarbonyl)amino)]-2-(4-{[(2,4-dimethylbenzoyl) oxy]methyl}phenyl)propanoic acid (8) (2.3 g, 5.5 mmol) in DMF (33 mL) cooled to 0 ¡ãC was added 6-aminoisoquinoline (1.0 g, 7.1 mmol) and 2,4,6-trimethylpyridine (947 muL, 7.1 mmol). After 10 min at 0 ¡ãC, a solution of 2,2,2-trichloro-1,1-dimethylethyl chloroformate (1.7 g, 7.1 mmol) in DMF (8.6 mL) was added and the reaction stirred at 0 ¡ãC for 2 h. The mixture was poured into NaHCO3 (sat.)/EtOAc and extracted with EtOAc. The organic layers were then washed with NaCl (sat.), dried (Na2SO4) filtered and evaporated. Column chromatography (70percent EtOAc/hexanes) gave pure (S)-4-{3-[(tert-butoxycarbonyl) amino]-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl}benzyl 2,4-dimethylbenzoate (9) (1.93 g, 63percent, 98percent ee) as a off-white solid. Recrystallization from EtOAc/hexanes gave 9 (1.43 g, 47percent, 99.7percent ee, S,SWhelk-01) as a off-white crystalline solid. Mp 155-156 ¡ãC. IR (ATR): 1713, 1644, 1527 cm-1. 1H NMR (500 MHz, DMSO-d6): delta = 9.14 (s, 1H), 8.39 (d, J = 5.7 Hz, 1H), 8.38 (s, 1H), 8.02 (d, J = 8.7 Hz, 1H), 7.75 (d, J = 7.9 Hz, 1H), 7.69- 7.66 (m, 2 H), 7.43 (s, 4 H), 7.11 (s, 1H), 7.07 (d, J = 8.4 Hz, 1H), 7.02 (br t, J = 5.4 Hz, 1H), 5.25 (s, 2 H), 4.13-4.10 (m, 1H), 3.58-3.53 (m, 1H), 3.34-3.30 (m, 1H), 2.49 (s, 3 H), 2.29 (s, 3 H), 1.32 (s, 9 H). 13C NMR (125 MHz, DMSO-d6): delta = 171.0, 166.4, 155.8, 151.5, 143.2, 142.4, 140.4, 139.5, 137.8, 136.1, 135.2, 132.3, 130.4, 128.5, 128.1, 128.0, 126.6, 126.1, 125.0, 121.0, 120.0, 113.1, 77.8, 65.6, 51.7, 42.9, 28.2, 21.2, 20.8. LC-MS (ES+): m/z = 554 [M + 1]+, 576 [M + 23]+. Anal Calcd for C33H35N3O5: C, 71.59; H, 6.37; N, 7.59. Found: C, 71.54; H, 6.51; N, 7.58.

23687-26-5, The synthetic route of 23687-26-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Delong, Mitchell A.; Sturdivant, Jill M.; Synthesis; vol. 51; 4; (2019); p. 953 – 959;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

13130-79-5, 1-Bromoisoquinolin-3-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of l-bromoisoquinolin-3-amine (400 mg, 1.79 mmol, 1.00 eq) and e/-Z-butoxycarbonyl tert-butyl carbonate (3.91 g, 17.9 mmol, 4.12 mL, 10.0 eq) was stirred at 70 C for 16 hours. The residue was purified by column chromatography (Si02, diethyl ether/ethyl acetate = 5: 1) to give /er -butyl N-(l -bromo-3-isoquinolyl) carbamate (400 mg, 1.24 mmol, 69.2 % yield) as a yellow solid. ESI MS m/z 322.1 , 324.1 [M+H]+ .

13130-79-5, As the paragraph descriping shows that 13130-79-5 is playing an increasingly important role.

Reference£º
Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; MARX, Matthew, Arnold; BLAKE, James, F.; FELL, Jay, Bradford; FISCHER, John, P.; MEJIA, Macedonio, J.; (164 pag.)WO2020/47192; (2020); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

63927-23-1, 5-Bromo-8-nitroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

63927-23-1, Iodomethane (506 mmol) was added to a solution of 5-bromo-8-nitroisoquinoline (101 mmol) inN,N-dimethylformamide (200 mL) and the reaction mixture was maintained for 16 h at 40 C. The precipitated solids were collected by filtration, washed with ether (2 x 250 mL), and dried to provide 5- bromo-8-nitro-N-methylisoquinolinium iodide in 83% yield as a red solid.

63927-23-1 5-Bromo-8-nitroisoquinoline 816983, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2009/23844; (2009); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.151004-88-5,(R)-N-Cbz-3,4-dihydro-1H-isoquinolinecarboxylic acid,as a common compound, the synthetic route is as follows.

To N-Benzyloxycarbonyl-D-1,2, 3, 4-tetrahydro-isoquinoline-1-carboxylic acid (3.11 g, 10 mmol, made from commercially available D-1,2, 3, 4-tetrahydro- ISOQUINOLINE-1-CARBOXYLIC acid and O-BENZYLOXYCARBONYL-N-HYDROXYSUCCINAMIDE) in THF (10 mL) was added BH3 (1M solution in THF; 30 mL, 30 mmol) over 5 min, and the reaction mixture was stirred for 3 hours. Acetic acid (9 mL) in MEOH (90 mL) was added and the mixture was stirred for 30 min. Solvents were evaporated, the residue was taken up in EtOAc and was washed with saturated aqueous NAHC03 (90 mL, aq. phase pH 7-8) and brine. The organic layer was dried over NA2S04 and concentrated to give compound 13a (2.97 g, 100%). MS (CI) M/Z 253.9 (MH+-CO2), 297. 9 (MH+) ; TR = 2.695 min (method 4)., 151004-88-5

The synthetic route of 151004-88-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2005/7164; (2005); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem