Heterocyclic Building Blocks-Isoquinoline

679433-91-1, 5-Bromo-8-methoxyisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,679433-91-1

To a mixture of l-bromo-5-methoxynaphthalene1 (320 mg, 1.3 mmol) and 4-aminophenylboronic acid (HCl salt, 320 mg, 1.85 mmol) in dioxane (3 mL)-H20 (3 mL) was added PdCl2(dppf)-dichloromethane (53 mg, 0.063 mmol) and Na2CO3 (530 mg, 4.2 mmol). The mixture was heated to 1000C for 12 h and cooled to room temperature. The mixture was extracted with dichloromethane and the organic phase was dried over Na2SO^ concentrated, and purified on silica with 5% (2N NH3 in MeOH) in dichloromethane to afford the product as a tan solid (300 mg, 89%). MS (ESI pos. ion) m/z: 251 (M+H).

As the paragraph descriping shows that 679433-91-1 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; WO2007/5668; (2007); A2;,
Isoquinoline – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105627-79-0,Isoquinoline-5-sulfonyl chloride hydrochloride,as a common compound, the synthetic route is as follows.

Reference Preparation Example Homopiperazine (3.413 g) was dissolved in tetrahydrofuran (57 ml) with stirring. After cooling the solution to -5 C, 5-isoquinolinesulfonyl chloride hydrochloride (3.00 g) was added while maintaining the intemal temperature at 10 C or less. The mixture was stirred at 5 C or less for four hours. The reaction mixture was allowed to stand to reach room temperature and filtered to remove insoluble matter. The filtrate was concentrated under reduced pressure, followed by the addition of ethyl acetate (57 ml), water (17 ml), and 3 N hydrochloric acid aqueous solution (6.4 ml). The mixture was separated into layers to obtain a water layer. After washing the water layer with ethyl acetate (7 ml), water (6 ml), ethyl acetate (57 ml), and 6 N sodium hydroxide aqueous solution (3 ml) were added to separate the mixture into layers and obtain an organic layer. The organic layer was concentrated under reduced pressure and the residue was dried under reduced pressure to obtain fasudil (1.36 g). The yield was 41%. The fasudil is processed by the method described in JP-A-9-71582 to obtain fasudil hydrochloride. Fasudil can also be obtained in the same manner using the solvents listed below instead of tetrahydrofuran used in the Reference Preparation Example at yields described in the parentheses. Acetone (22%), acetonitrile (30%), 1,2-dimethoxyethane (31%), 2-butanone (24%), anisole (34%), isopropyl ether (10%), ethyl acetate (38%), toluene (18%), etc. Concentration of the filtrate was unnecessary when anisole, isopropyl ether, ethyl acetate, and toluene were used as the solvent., 105627-79-0

As the paragraph descriping shows that 105627-79-0 is playing an increasingly important role.

Reference£º
Patent; Asahi Kasei Pharma Corporation; EP1726306; (2006); 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.1532-97-4,4-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

4-Bromo-5-nitroisoquinoline (11). Potassium nitrate (5.34 g; 0.052 mol) was added to 20 mL of concentrated sulfuric acid and slowly dissolved by careful heating. The resulting solution was added dropwise to a solution of 4-bromoisoquinoline (10 g, 0.048 mol) dissolved in 40 mL of the same acid at O0C. After removal of the cooling bath, the solution was stirred for one hour at room temperature. The reaction mixture was then poured onto crushed ice (400 g) and made basic with ammonium hydroxide. The resulting yellow precipitate was collected by filtration and the filtrate was extracted with diethyl ether (3 x 500 mL), dried (Na2SO4), and concentrated to give a yellow solid that was combined with the initial precipitate. Recrystallization from methanol gave 12.1 g (89percent) of 11 as slightly yellow crystals

1532-97-4, The synthetic route of 1532-97-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DARPHARMA, INC.; WO2006/12640; (2006); 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.3336-43-4,1-Chloroisoquinolin-4-ol,as a common compound, the synthetic route is as follows.

Step 1: Preparation of 1-chloro-4-ethoxyisoquinoline To a solution of 1-chloroisoquinolin-4-ol (1.0 g, 5.5 mmol) in acetonitrile (10 mL) was added K2CO3 (2.3 g, 16.7 mmol) followed by ethyl iodide (0.87 ml, 11.0 mmol) at room temperature. The reaction mixture was stirred at room temperature for overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-4-ethoxyisoquinoline (0.7 g, 62%) as off-white solid. 1H NMR (400 MHz, CD3OD): delta ppm 8.26-8.24 (m, 2H), 7.79 (s, 1H), 7.76-7.26 (m, 2H), 4.29-4.24 (q, J=6.8 Hz, 2H), 1.58-1.54 (t, J=6.8 Hz, 3H); MS: MS m/z 207.7 (M++1)., 3336-43-4

As the paragraph descriping shows that 3336-43-4 is playing an increasingly important role.

Reference£º
Patent; Bristol-Myers Squibb Company; Rajamani, Ramkumar; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Meanwell, Nicholas A.; Scola, Paul Michael; US2013/142754; (2013); A1;,
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1350643-72-9, (S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a mixture of compound (C-3) (3.0 mmol, 1.0 eq) and 2,4-dichloro-3-nitropyridine (3.0 mmol, 1.0 eq) in EtOH (10 mL), triethylamine (6.0 mmol, 2.0 eq) is added and the resulting mixture is stirred at reflux overnight. The mixture is allowed to cool to RT and then concentrated in vacuo. The resultant residue is purified by flash column chromatography on silica gel (1% MeOH-DCM) to afford the product (I-1)., 1350643-72-9

1350643-72-9 (S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 66607319, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12918; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34784-05-9,6-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

Specific preparation methods are: no special protection, clean air to a single-necked flask were added sequentially magneton, 6-bromo-isoQuinoline (83.2mg, 0.4mmol), added elemental iodine (20mg, 20mol%), 70% of the mass fraction of the water phase of t-butylperoxyHydrogen (152mg, 1.2mmol), then add toluene (728.8mg, 8mmol), toluene as both reactant and as a solvent, at 150 After 1 hour TLC showed the starting material 6-bromo-isoquinoline consumed completely. Heating was stopped to quench the reaction. Without CraftsTake on a wet sample directly, 200-300 mesh silica gel column chromatography, a mixed solvent of ethyl acetate and petroleum ether (1: 6) rinse. SeparateA compound of formula VIIIa structural formula 92.6mg, 74% yield;

34784-05-9, As the paragraph descriping shows that 34784-05-9 is playing an increasingly important role.

Reference£º
Patent; Xiangtan University; Yang, Luo; Luo, Wenkun; (17 pag.)CN105503724; (2016); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.164148-92-9,tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.

Acetic acid 2-{6-[(4′-trifluoromethylbiphenyl-2carbonyl)-amino]-3,4-dihydro-1H -isoquinolin-2-yl}-ethyl ester Acetyl chloride (100 mg, 1.25 mmole) and 4-dimethylaminopyridine (700 mg, 5.7 mmole) were combined in 5 mL of toluene and the mixture was cooled to 0 C. in an ice bath. To this mixture was added a solution of Compound 67 from Example 6 (500 mg, 1.14 mmole) in 3 mL of methylene chloride. The reaction was allowed to warm to ambient temperature and was stirred under a nitrogen atmosphere for 2 hrs. The reaction was washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine and then dried over magnesium sulfate. Purification of the residue obtained on evaporation was accomplished with silica gel chromatography using 3% methanol in ethyl acetate as the eluent. MS (Cl): 483 (M+H+) 1 H NMR (400 MHz, DMSO) delta4.25 (dd, 2H); 3.62 (s, 2H); 2.78 (m, 6H); 2.06 (s, 3H).

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; Pfizer Inc; US6121283; (2000); A;,
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Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3336-60-5,1-Chloro-4-methoxyisoquinoline,as a common compound, the synthetic route is as follows.

6-Chloro-1, 3-Oxazino [5,6-c] isoquinoline was prepared by the procedure of Miyoko Toyama and Hirotaka Otomasu starting from1-chloro-4-hydroxy isoquinoline. The starting material: 1-chloro-4-hydroxy isoquinoline (Example 226c) was prepared by the synthetic sequence shown above. MCPBA oxidation of 4-methoxy isoquinoline (Example 222a) was carried as usual to give 79.1percent of the corresponding N-oxide (Example 226a). The material was converted into the 1-chloro derivative immediately afterward in POCI3 to give the chloride (Example 226b) in essentially quantitative yield. The crudel-chloro-4-methoxy isoquinoline was de-methylated in BBr3 at room temperature to give the corresponding 1-chloro-4-hydroxy isoquinoline (Example 226c) after treating the crude BBr3 mixture with anhydrous methanol at room temperature, followed by evaporation to get rid of excess of borate residues. The reaction of Miyoko Toyama and Hirotaka Otomasu gave 266mg of 6-chloro-1, 3- oxazino [5,6-c] isoquinoline (Example 226d, 62.3percent) overall yield from 300mg of 4- methoxy isoquinoline in 4 steps. LC/MS Rt-min([M-HCHO] H+) [method D]: 2.45(192).’H NMR (400 MHz, CHLOROFORM-D)8 ppm 5.02 (s, 2 H) 5.41 (s, 2 H) 7.68 (m, 1 H) 7.77 (ddd, J=8. 25,6. 91,1. 22 Hz, 1 H) 8.10 (d, J=8. 31 Hz, 1 H) 8.26 (d, J=8. 56 Hz,1 H). The chloride was found to be unreactive under the alkylation protocol of Example 184. The corresponding 6-fluoro-1, 3-oxazino [5,6-c] isoquinoline (Example 226) was prepared by the method of [Uchibori, Y.; Umeno, M.; Yoshiokai, H.; Heterocycles, 1992,34 (8),1507-1510] cited earlier. The reaction was not allowed to go to completion, and the crude reaction mixture was recovered as a mixture of ratio of 1: 2.4 (Cl : F). Without further purification, the chloride/fluoride mixture was alkylated with the tripeptide using the procedure of Example 184 to give 66mg (50.0percent) of BOCNH-P3(L-t-BuGly)-P2 [ (4R)- ( 1, 3-oxazino [5,6-c] isoquinoline-6-oxo)-S-proline]-P1 (lR, 2S VinylAcca)-CONHSO2Cyclopropane after preparative HPLC purification. LC/MS Rt-min(MNa+) [method D]: 3.03(764).’H NMR (400 MHz, CD30D)8 ppm 1.01 (s, 9 H) 1.06 (dd, J=8. 07,1. 96 Hz, 2 H) 1.22 (s, 10 H) 1.34 (d, J=6. 11 Hz,1 H) 1.42 (m, 1 H) 1.86 (dd, J=8. 07,5. 38 Hz,1 H) 2.23 (m, 2 H) 2.59 (dd,J=13. 82,6. 97 Hz,1 H) 2.93 (m,1 H) 4.03 (dd,J=11. 86,3. 06 Hz,1 H) 4.23 (s, 1 H) 4.41 (d,J=11. 98 Hz,1 H) 4.50 (dd, J=9. 66,6. 97 Hz,1 H) 4.87 (m, 2 H) 5.11 (d, J=10. 52 Hz, 1 H) 5.28 (d,J=17. 12 Hz,1 H) 5.34 (s, 2 H) 5.74 (m, 2 H) 7.51 (t, J=7. 46 Hz,1 H) 7.70 (t, J=7. 58 Hz,1 H) 7.95 (d, J=8. 31 Hz, 1 H) 8.12 (d, J=8. 31 Hz,1 H)., 3336-60-5

As the paragraph descriping shows that 3336-60-5 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99274; (2003); A1;,
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Isoquinoline | C9H7N – PubChem

891782-60-8,891782-60-8, 7-Bromo-3,4-dihydro-2H-isoquinolin-1-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Sodium hydride (57.1 mg, 1.43 mmol, 60% in oil) was suspended in DMF (3mL) at 0 C, and 7-bromo-3,4-dihydroisoquinolin-1(2B)-one (215 mg, 0.951 mmol) wasadded. After stirring for 10 mm, 1 -(chloromethyl)-4-methoxybenzene (0.155 mL, 1.14mmol) was added. The reaction mixture was stirred at rt for 1 h, then quenched withsaturated NH4C1 and extracted with EtOAc (3x). The combined organics were combined and concentrated to give a light yellow crystalline solid. The crude was purified by flash chromatography to give 287A (265 mg, 80.5%) as a colorless oil. MS(ESI) m/z 347.8 (M+2+H).

As the paragraph descriping shows that 891782-60-8 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne, M.; SHAW, Scott, A.; HALPERN, Oz, Scott; HU, Carol, Hui; KICK, Ellen, K.; (311 pag.)WO2017/40449; (2017); 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.164148-92-9,tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.

Step-1: Synthesis of tert-butyl 6-(2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a stirred solution of 2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (300 mg, 0.84 mmol, 1.0 eq) in toluene (5 mL) was added m-CPBA (361 mg, 2.10 mmol, 2.5 eq) and allowed to stir at RT for 30 min. tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (208 mg, 0.84 mmol, 1.0 eq) and DIPEA (433 mg, 3.36 mmol, 4.0 eq) were added and allowed to stir at RT for 12 h. Progress of reaction was monitored by LCMS. After completion of reaction, precipitated compound was filtered off, washed with toluene (3 mL) and dried under reduced pressure to obtain tert-butyl 6-(2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate (220 mg, 47.00%).

164148-92-9, 164148-92-9 tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate 2756371, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Isoquinoline – Wikipedia
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