Category: 486-73-7

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.486-73-7,Isoquinoline-1-carboxylic acid,as a common compound, the synthetic route is as follows.

Isoquinoline carboxylic acid a (5.0 g, 28.9 mmol), N.O-dimethy-hydroxylamine hydrochloride (3.1 g, 31.8 mmol) EDC (6.1 g, 32 mmol), DIPEA (5.7 mL, 32 mmol) and MeCN (50 mL) were mixed together and stirred at rt overnight. The MeCN was removed under reduced pressure and the residue partitioned between water (200 mL) and EtOAc (200 mL). The phases were separated and the aqueous phase was extracted with EtOAc (2 x 50 mL). The combined organic phases were b as a colorless solid.

486-73-7, The synthetic route of 486-73-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GENENTECH, INC.; WO2006/69063; (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.486-73-7,Isoquinoline-1-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: 2-Pyridinecarboxylic, 2-quinolinecarboxylic or 1-isoquinolinecarboxylic acid (1.5 mmol) and NEt3 (1.5 mmol,152 mg, 209 mL) were added to dry NMP (2.1 mL) in a Schlenk flaskunder Ar atmosphere. At 0 C, diphenyl phosphoryl azide(1.6 mmol, 440 mg, 345 mL) was added drop-wise and the reactionmixture was stirred at 35 C for 1 h. N-Oxide (1 mmol) was thenadded in one portion and the reaction mixture was stirred at 70 Cfor 20 h. The mixture was then poured into water (50 mL) andextracted with AcOEt (3 x 20 mL). Combined organic extracts werewashed with brine (5 x 30 mL) dried over anhyd. Na2SO4 andevaporated. Products 2 were purified by column chromatographyon silica gel using hexaneseAcOEt 2:1 or tolueneeAcOEt 2:1, thenAcOEt as eluent.

486-73-7, The synthetic route of 486-73-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Bukowska, Patrycja; Piechowska, Joanna; Loska, Rafa?; Dyes and Pigments; vol. 137; (2017); p. 312 – 321;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

486-73-7, Isoquinoline-1-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1-Hydroxybenzotriazole hydrate (1.47 equiv of acid), N-ethyl-N’-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.47 equiv of acid), N,N-diisopropylethylamine (3.45 equiv of acid), and corresponding acid were added to a solution of compound 10 (1.0 equiv of acid) in dichloromethane (0.1 M). The reaction mixture was stirred at room temperature for 12 h and then washed with water. The separated organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was purified with silica gel column chromatography to afford compound 11., 486-73-7

The synthetic route of 486-73-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Lee, Seung Kyu; Choi, Kwang Hyun; Lee, Sang Jae; Lee, Jong Sun; Park, Ji Yun; Kim, B. Moon; Lee, Bong Jin; Bioorganic and Medicinal Chemistry Letters; vol. 21; 1; (2011); p. 133 – 136;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

486-73-7, Isoquinoline-1-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(Step 1) Synthesis of methyl (3-chloro-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate In DMF (15 ml) were dissolved 1-isoquinolinecarboxylic acid (1.00 g, 5.77 mmol), methyl 4-amino-3-chlorophenylacetate (1.23 g, 6.16 mmol), HOBt (0.16 g, 1.15 mmol), and DMAP (0.14 g, 1.15 mmol). To the resulting solution was added EDC HCl (1.33 g, 6.93 mmol), followed by stirring at room temperature for 14 hours. The reaction mixture was poured into water (40 ml). The crystals precipitated were collected by filtration under reduced pressure, washed with water and ether, dried under reduced pressure to give methyl (3-chloro-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate (1.14 g, 56%) as a brown solid. 1H-NMR (CDCl3) delta: 3.62 (s, 2H), 3.72 (s, 3H), 7.29 (m, 1H), 7.40 (d, J=1.9Hz, 1H), 7.71-7.78 (m, 2H), 7.88-7.91 (m, 2H), 8.58 (d, J=5.4Hz, 1H), 8.65 (d, J=8.3Hz, 1H), 9.71 (m, 1H), 11.02 (m, 1H). MS (ESI) m/z 355 (M++1).

486-73-7, The synthetic route of 486-73-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1346982; (2003); 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.486-73-7,Isoquinoline-1-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: At 0C, to a solution of 1.0 mmol of isoquinoline- 1 -carboxylic acid in anhydrous THF(20mL),0.135g(1.0mmol) of HOBt and 1.0 mmol of (2S,3R)- 2-Amino-3-hydroxy-N-octylbutanamide, (2S,3R)-2-Amino-3-hydroxy-N- dodecylbutanamide, (2S,3R)-2-Amino-3-hydroxy-N-tetradecylbutanamide, or (2S,3R)-2-Amino-3-hydroxy-N-octadecylbutanamide were added. After 5 min, 0.220g (1.1 mmol) of EDOHC1 was added, and the pH of the solution was adjusted to 8-9 with 4-methylmorpholine. The mixture was stirred at 0 C for 2 h and at room temperature overnight. On evaporation the residue was dissolved in 80 mL of ethyl acetate. The solution was washed successively with saturated sodium bicarbonate, 5% potassium bisulfate, and saturated sodium chloride, and the organic phase was separated and dried over anhydrous magnesium sulfate for 2 h. After filtration and evaporation under reduced pressure crude product was obtained and recrystallized using ethyl acetate to obtain compounds NZJUlf, NZJU2f, NZJU3f, and NZJU4f. N-((2S,3R)-3-hydroxy- 1-oxo- 1 -(octylamino)butan-2-yl)- isoquinoline- 1 -carboxamide (NZJUlf) was obtained in a yield of 0.258 g (67.0%) as colorless powder. XH NMR (300 MHz, CDC13) delta 9.51 (d, J= 8.1 Hz, 1H), 9.08 (d, J= 8.0 Hz, 1H), 8.52 (d, J= 5.5 Hz, 1H), 7.92 – 7.79 (m, 2H), 7.79 – 7.61 (m, 2H), 6.89 (s, 1H), 4.66 – 4.46 (m, 2H), 3.32 – 3.1 1 (m, 2H), 1.56 – 1.42 (m, 2H), 1.34 – 1.04 (m, 13H), 0.82 (t, J= 6.7 Hz, 3H); 13C NMR (75 MHz, CDC13) delta 171.4, 167.5 , 147.2, 140.6, 137.5, 130.6, 128.8, 127.3, 127.0, 124.8 , 66.6, 56.9, 39.6, 31.7, 29.4, 29.2, 26.9, 22.6, 18.6, 14.1; ESI/MS (m/e) 386.20 [M+H]+; Anal. Calcd. For C22H31N3O3: C, 68.54; H, 8.1 1; N, 10.90%. Found: C, 68.47; H, 8.24; N, 10.86%. N-((2S,3R)-3-hydroxy- 1-oxo- 1 -(dodecylamino)butan-2-yl)- isoquinoline- 1 -carboxamide (NZJU2f) was obtained in a yield of 0.310 g (70.3%) as colorless powder. XH NMR (300 MHz, CDC13) delta 9.51 (d, J= 7.6 Hz, 1H), 9.08 (d, J= 7.8 Hz, 1H), 8.52 (d, J= 5.2 Hz, 1H), 7.95 – 7.80 (m, 2H), 7.80 – 7.62 (m, 2H), 6.89 (s, 1H), 4.67 – 4.45 (m, 2H), 3.35 – 3.09 (m, 2H), 1.57 – 1.41 (m, 2H), 1.37 – 0.98 (m, 21H), 0.87 (t, J= 6.4 Hz, 3H); 13C NMR (75 MHz, CDC13) delta 171.4, 167.3 , 147.3, 140.6, 137.4, 130.5, 128.8, 127.3, 127.0, 124.7, 66.6, 56.9, 39.6, 31.9, 29.6, 29.5, 29.4, 29.3, 26.9, 22.7, 18.6, 14.1; ESI/MS (m/e) 442 [M+H]+; Anal. Calcd. For C26H39N303: C, 70.71; H, 8.90; N, 9.52%. Found: C, 70.68; H, 8.86; N, 9.49%. N-((2S,3R)-3-hydroxy- 1-oxo- 1 -(tetradecylamino)butan-2-yl)- isoquinoline-1 -carboxamide (NZJU3f) was obtained in a yield of 0.317 g (67.6%) as colorless powder. XH NMR (300 MHz, CDC13) delta 9.51 (d, J= 8.3 Hz, 1H), 9.07 (d, J= 8.1 Hz, 1H), 8.52 (d, J= 5.5 Hz, 1H), 7.94 – 7.79 (m, 2H), 7.78 – 7.60 (m, 2H), 6.89 (s, 1H), 4.68 – 4.46 (m, 2H), 3.35 – 3.1 1 (m, 2H), 1.58 – 1.39 (m, 2H), 1.39 – 1.00 (m, 25H), 0.88 (t, J= 6.4 Hz, 3H); 13C NMR (75 MHz, CDC13) delta 171.2, 167.2 , 147.4, 140.6, 137.4, 130.5, 128.7, 127.3, 127.0, 124.7 , 66.7, 57.2, 39.6, 31.9, 29.7, 29.6, 29.4, 29.3, 28.3, 26.9, 22.7, 18.6, 14.1; ESI/MS (m/e) 470 [M+H]+; Anal. Calcd. For C28H43 3O3: C, 71.61 ; H, 9.23; N, 8.95%. Found: C, 71.58; H, 9.19; N, 8.98%. N-((2S,3R)-3-hydroxy- 1-oxo- 1 -(octadecylamino)butan-2-yl)- isoquinoline- 1 -carboxamide (NZJU4f) was obtained in a yield of 0.409 g (77.3%) as colorless powder. XH NMR (300 MHz, CDC13) delta 9.46 (d, J= 8.3 Hz, 1H), 9.08 (d, J= 7.4 Hz, 1H), 8.52 (d, J= 5.2 Hz, 1H), 7.94 – 7.83 (m, 2H), 7.81 – 7.62 (m, 2H), 6.95 (s, 1H), 4.68 – 4.47 (m, 2H), 3.37 – 3.15 (m, 2H), 1.54 – 1.40 (m, 2H), 1.38 – 1.00 (m, 33H), 0.88 (t, J= 6.2 Hz, 3H); 13C NMR (75 MHz, CDC13) delta 171.5, 167.4 , 147.4, 140.5, 137.4, 130.6, 128.8, 127.3, 127.0, 124.7, 66.7, 57.0, 39.6, 31.9, 29.7, 29.6, 29.4, 29.3, 26.9, 22.7, 18.6, 14.1; ESI/MS (m/e) 526 [M+H]+; Anal. Calcd. For C32H51N3O3: C, 73.10; H, 9.78; N, 7.99%. Found: C, 73.07; H, 9.86; N, 8.02%.

486-73-7, The synthetic route of 486-73-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ZHEJIANG UNIVERSITY; GEORGIA REGENTS RESEARCH INSTITUTE, INC.; LIU, Feiyan; LIU, Kebin; HUANG, Zhizhen; WU, Ping; WO2014/66613; (2014); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem