Heterocyclic Building Blocks-Isoquinoline

23687-25-4,23687-25-4, Isoquinolin-4-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 76; N-(Isoquinolin-4-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide; (1) 2,2,2-Trichloroethyl isoquinolin-4-ylcarbamate; To a solution of 3-aminoisoquinoline (1.00 g; 6.94 mmol) and pyridine (0.660 ml, 8.32 mmol) in tetrahydrofuran (23 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.15 ml, 8.32 mmol), and the mixture was stirred at room temperature for 1 hour and half. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was poured to the residue, and 2.03 g (91.7%) of the desired product as a solid was separated by filtration. 1H-NMR (DMSO-d6) delta; 5.01 (2H, s), 7.54 (1H, t, J = 7.8 Hz), 7.72 (1H, t, J = 7.8 Hz), 7.91 (1H, d, J = 7.8 Hz), 8.06 (1H, d, J = 8.1 Hz), 8.17 (1H, s), 9.15 (1H, s).

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

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
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.80278-67-7,Isoquinoline-5-carbaldehyde,as a common compound, the synthetic route is as follows.

80278-67-7, General procedure: General procedure (14): In a dry sealed tube, a quinoline/isoquinoline-carboxaldehyde derivative (1.0 equiv) and a gramine derivative (1.0 equiv) were dissolved in anhydrous acetonitrile (3 mL for 0.530 mmol of gramine derivative). Tributyllphosphine (2.25 equiv) was added and the sealed reaction was heated at 90 ¡ãC in an oil bath for 22 h. After the reaction was allowed to cool to room temperature, the solvent was removed under vacuum. The crude material was washed with methanol and diethyl ether to afford the alkene product as a yellow precipitate which was filtered and dried under vacuum. Chemical Example 25 5-((E)-2-(1/-/-indol-3-vl)vinyl)isoquinoline Compound 25 [a166] (40 mg, 0.148 mmol) was prepared as a yellow solid from Intermediate 23 (92 mg, 0.530 mmol) and isoquinoline-5-carboxaldehyde (83 mg, 0.530 mmol) according to general procedure (14). Yield: 28percent. 1H NMR (400 MHz, Acetone) delta: 10.57 (s, 1 H), 9.28 (d, J = 0.8 Hz, 1 H), 8.56 (d, J = 6.0 Hz, 1 H), 8.22 (d, J = 6.0 Hz, 1 H), 8.17 – 8.11 (m, 2H), 7.98 (d, J = 8.2 Hz, 1 H), 7.90 (d, J = 16.2 Hz, 1 H), 7.78 (d, J = 2.5 Hz, 1 H), 7.69 (t, J = 7.7 Hz, 1 H), 7.62 (d, J = 16.2 Hz, 1 H), 7.53 – 7.47 (m, 1 H), 7.29 – 7.14 (m, 2H). 13C NMR (100 MHz, Acetone) delta: 154.07, 151.28, 147.70, 143.48, 138.48, 136.75, 129.59, 128.49, 127.67, 126.60, 124.40, 123.17, 121.19, 120.89, 116.74, 116.54, 115.67, 112.82. LC-MS (ESI): m/z 272.1 [M + H]+.

The synthetic route of 80278-67-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NATIONAL UNIVERSITY OF SINGAPORE; LEE, Sang Hyun; DYMOCK, Brian William; KITAGAWA, Mayumi; SEE, Cheng Shang; (178 pag.)WO2016/200339; (2016); A1;,
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52986-70-6, 6-Methoxyisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

52986-70-6, General procedure: Under air, isoquinoline derivatives 1 (2.0 mmol) and bromoacetyl derivatives 2 (2.2 mmol) were mixed and stirred in THF (5 mL) at r.t. for 4 h; then THF was removed under vacuum and EtOH (5 mL), methyl perfluoroalk-2-ynoates 3 (1.0 mmol), and DIPEA (1.0 mmol) were added. The resulted mixture continued to be stirred at r.t. for another 7 h. EtOH was removed as before and the residue was purified by column chromatography on silica gel by eluting with petroleum ether / ethyl acetate 20:1) to afford the desired product 4.

As the paragraph descriping shows that 52986-70-6 is playing an increasingly important role.

Reference£º
Article; Zhou, Wei; Liu, Hao; Guo, Yongyi; Gu, Yiting; Han, Jing; Chen, Jie; Deng, Hongmei; Shao, Min; Zhang, Hui; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 222-223; (2019); p. 51 – 58;,
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190777-77-6, 5-Bromoisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0461] To 5-bromoisoquinolin- 1 (2H)-one (40 mg, 0.18 mmol) in dioxane (1 mL) was added bis(pinacolato)diboron (63 mg, 0.25 mmol), and PdC12[P(Ph)3]2 (6 mg, 0.01 mmol). The reaction mixture sealed and heated to 100 C for lh. The reaction was cooled to room temperature and telescoped to the next reaction. MS (m/z) 272.3 [M+H]., 190777-77-6

As the paragraph descriping shows that 190777-77-6 is playing an increasingly important role.

Reference£º
Patent; GILEAD SCIENCES, INC.; BRIZGYS, Gediminas; CANALES, Eda; CHOU, Chien-hung; GRAUPE, Michael; HU, Yunfeng, Eric; LINK, John, O.; LIU, Qi; LU, Yafan; SAITO, Roland, D.; SCHROEDER, Scott, D.; SOMOZA, John, R.; TSE, Winston, C.; ZHANG, Jennifer, R.; WO2014/134566; (2014); A2;,
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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

Compound 1 was prepared in 3 steps from compound A according to the following procedures:Compound A was coupled to 2-((tert-butoxycarbonyl)amino)pyrazolo [1,5 -ajpyrimidine-3-carboxylic acid according to the following procedure: Compound A (27.4 mmol, 1.0 equiv), HOBt hydrate (1.2 equiv), 2-((tert- butoxycarbonyl)amino)pyrazolo [1 ,5-a]pyrimidine-3-carboxylic acid (1.05 equiv) and EDCI (1.25 equiv) were added to a 200 mL round bottomed flask with a stir bar. N,N-Dimethylfonnamide (50 mL) was added and the suspension was stirred at RT for 2 mi Hunig?s base (4.0 equiv) was added and after which the suspension became homogeneous and was stirred for 22h resulting in the formation of a solid cake in the reaction flask. The solid mixture was added to water (600 mL) and stirred for 3h. The resulting cream colored solid was filtered and washed with water (2 x 100 mL) and dried. The solid was then dissolved in methylene chloride (40 mL) after which trifluoroacetic acid (10 equiv, 20 mL) was added and the reaction was stirred for 30 mm at RT after which there is no more starting material by LC/MS analysis. The solution was then concentrated and coevaporated with a mixture of methylene chloride/ethanol (1:1 v/v) and then dried under high vacuum ovemight. The resulting solid was triturated with 60 mL of ethanol for lh and then collected via vacuum filtration. The beige solid was then neutralized with sodium carbonate solution (100 mL) and then transferred to a separatory funnel with methylene chloride (350 mL). The water layer was extracted with an additional 100 mL of methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum to provide a pale yellow solid that was purified using flash silica gel chromatography (Combiflash, 24g column, gradient of 0- 5% methanol/methylene chloride) to provide amide B. ESI-MS m/z: 459.4 [M+Hj+., 1350643-72-9

As the paragraph descriping shows that 1350643-72-9 is playing an increasingly important role.

Reference£º
Patent; INFINITY PHARMACEUTICALS, INC.; CRENIER, Louis; LESCARBEAU, Andre; SHARMA, Praveen; GENOV, Daniel G.; (324 pag.)WO2017/48702; (2017); A1;,
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50458-79-2, Ethyl 3-isoquinolinecarboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,50458-79-2

General procedure: To the solution of ester (10 mmol) in THF (20 mL) and ethyl acetate (70 mmol), LiHMDS (30 mmol) was added very quickly at -40 C, and stirred at this temperature for 20 min. After completion of the reaction, reaction mixture was quenched with acetic acid (50 mmol) and then basified using 10% NaHCO3 solution, extracted with ethyl acetate (2¡Á100 mL), the combined organic layer was washed with water and brine solution and dried over Na2SO4. The specific purification procedure for each compound has been included along with their characterization data.

As the paragraph descriping shows that 50458-79-2 is playing an increasingly important role.

Reference£º
Article; Venkat Ragavan; Vijayakumar; Rajesh; Palakshi Reddy; Karthikeyan; Suchetha Kumari; Bioorganic and Medicinal Chemistry Letters; vol. 22; 12; (2012); p. 4193 – 4197;,
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23687-26-5, 6-Aminoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 87 Preparation of benzylisoquinolin-6-ylcarbamate (E87) To 6-aminoisoquinoline in DMF at -40¡ã C. was added NaH and solution was warmed to 0¡ã C. for 30 minutes. Then benzylchloroformate was added and the reaction stirred at 0¡ã C. for 2 hours. The solution was quenched with AcOH, poured into NaHCO3(sat) and extracted with EtOAc, dried (Na2SO4), filtered and evaporated. Flash chromatography (SiO2 90percent EtOAc/Hex) gave benzylisoquinolin-6-ylcarbamate. (E87).

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

Reference£º
Patent; AERIE PHARMACEUTICALS, INC.; US2008/167340; (2008); 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.55270-27-4,4-Bromoisoquinolin-1-amine,as a common compound, the synthetic route is as follows.,55270-27-4

General procedure: To a solution of CuI (0.1 eq), Pd(PPh3)2Cl2 (0.05 eq) and compound7 (1 eq) in MeCN (5 mL) were added ArBr (Ar a, b, c, e, f, g,h, k, l) or ArI (Ar q, r, s, t) (3 eq) and trimethylamine (1.5 eq). Thereaction mixture was flushed with argon and sealed in a pressuretube. The reaction mixture was stirred at 80 C for 3-4 h. The reactionmixture was extracted with EtOAc, washed with water andbrine and concentrated in vacuo. The product was dissolved inMeOH (15 mL) at 60 C for 1 h. The organic solvent was removed invacuum. The crude mixture was purified by column chromatographyon silica gel to give 8a, 8b, 8c, 8e, 8f, 8g, 8h, 8k, 8l, 8q, 8r, 8s,8t.To a solution of ArI (Ar = n, p) (3 eq) in MeCN (5 mL) was addedtrimethylamine (5 mL). The mixture was stirred at room temperaturefor 1 h, after which time CuI (0.1 eq), Pd(PPh3)2Cl2 (0.05 eq)and compound 7 (1 eq) were added. The reaction mixture wasflushed with argon and sealed in a pressure tube. The reactionmixture was stirred at 50 C for 24 h. The reaction mixture wasextracted with EtOAc, washed with water and brine and concentratedin vacuum. The product was then dissolved in MeOH (15 mL)at 60 C for 1 h. The organic solvent was removed in vacuo. Thecrude mixturewas purified by column chromatography on silica gelto give 8n and 8p.

As the paragraph descriping shows that 55270-27-4 is playing an increasingly important role.

Reference£º
Article; Ma, Cong-Xuan; Lv, Wei; Li, Ya-Xin; Fan, Bing-Zhi; Han, Xu; Kong, Fan-Sheng; Tian, Jing-Chao; Cushman, Mark; Liang, Jian-Hua; European Journal of Medicinal Chemistry; vol. 169; (2019); p. 1 – 20;,
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1532-91-8, 4-Chloroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1532-91-8, To a solution of 4-chloroisoquinoline 16a (10.0 g, 61 mmol) in 55 mL concentrated sulfuric acid was added a solution of potassium nitrate (7.98 g, 79 mmol) in 69.0 mL concentrated sulfuric acid at -5 C. The resulting mixture was stirred at 0 C. for 1 h and then stirred at room temperature overnight. The reaction mixture was poured to 300 mL ice water, adjusted pH to 8 using solid Na2CO3, extracted with EtOAc (200 mL*2). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column chromatography (0-100% EtOAc/PE) to give 4-chloro-5-nitroisoquinoline 16b (11.2 g, white solid, yield: 88%). MS-ESI calc’d. [M+H]+ 209, found 209.

The synthetic route of 1532-91-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MEDSHINE DISCOVERY INC.; WU, Lingyun; YAO, Yuanshan; CHEN, Zhaoguo; CHEN, Shuhui; (69 pag.)US2017/37050; (2017); A1;,
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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.347146-33-2,1-Chloroisoquinolin-6-amine,as a common compound, the synthetic route is as follows.

Example 69 1-Chloro-6-(4-chlorobenzenesulfonylamino)isoquinoline The title compound was obtained by the procedure of Example 1, except using 6-amino-1-chloroisoquinoline (Preparation Example 23) and 4-chlorobenzenesulfonyl chloride. 1H-NMR (CDCl3) delta (ppm): 7.33 (1H, brs), 7.39 (1H, dd, J=2.0, 8.8 Hz), 7.44 (2H, d, J=8.8 Hz), 7.50 (1H, d, J=5.6 Hz), 7.58 (1H, d, J=2.0 Hz), 7.81 (2H, d, J=8.8 Hz), 8.24 (1H, d, J=5.6 Hz), 8.25 (1H, d, J=8.8 Hz). FAB-MS: 353., 347146-33-2

As the paragraph descriping shows that 347146-33-2 is playing an increasingly important role.

Reference£º
Patent; Haneda, Toru; Tsuruoka, Akihiko; Kamata, Junichi; Okabe, Tadashi; Takahashi, Keiko; Nara, Kazumasa; Hamaoka, Shinichi; Ueda, Norihiro; Wakabayashi, Toshiaki; Funahashi, Yasuhiro; Semba, Taro; Hata, Naoko; Yamamoto, Yuji; Ozawa, Yoichi; Tsukahara, Naoko; Owa, Takashi; US2003/144507; (2003); A1;,
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