Category: isoquinoline

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

Preparation of intermediate 235 was performed via 2 reactions as reported below.Reaction 1: N-bromosuccinimide (716 mg; 4.03 mmol) was added portionwise at 0C to a solution of t-Butyl-6-amino-3,4-dihydroisoquinoline-2-carboxylate (1 g; 4.03 mmol) inDCM (20 mL). The reactiocn mixture was stirred at room temperature for 2 hours, poured onto a 10% aqueous solution of K2C03 and extracted with DCM.Reaction 2: N-bromosuccinimide (2.08 g; 11.68 mmol) was added portionwise at 0C to a solution of t-Butyl-6-amino-3,4-dihydroisoquinoline-2-carboxylate (2.9 g; 11.68 mmol) inC (60 mL). The reaction mixture was stirred at room temperature for 2 hours, poured onto a 10% aqueous solution of K2C03 and extracted with DCM.The two residues were combined and purified by chromatography over silica gel (irregular SiOH, 80g; mobile phase: gradient from 20% EtOAc, 80% heptane to 40% EtOAc, 60%hetptane). The pure fractions were collected and evaporated to dryness yielding 2.8 g (54%) of intermediate 235.

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; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (419 pag.)WO2018/2219; (2018); 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

A solution of amine 1 (3.35 mmol, 1.0 equiv) in methylene chloride (40 mL) was cooled to 0 C. and charged with triethylamine (1.0 equiv) and trifluoroacetic anhydride (1.0 equiv). The resulting mixture was stirred for 15 min then partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic phase was separated, dried with sodium sulfate and concentrated to afford compound 251. ESI-MS m/z: 395.2 [M+H]+., 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; Intellikine LLC; Infinity Pharmaceuticals, Inc.; CASTRO, Alfredo C.; CHAN, Katrina; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LI, Liansheng; LIU, Tao; LIU, Yi; REN, Pingda; SNYDER, Daniel A.; TREMBLAY, Martin R.; US2013/267521; (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.164148-92-9,tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.

A toluene solution of 6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline (248 mg), 2-chlorobenzothiazole (186 mg), palladium acetate (22 mg), cesium carbonate (651 mg), and Xanphos (58 mg) was stirred at 120C for 1 hour under microwave irradiation. The reaction solution was purified by column chromatography to obtain the title compound (381 mg, quantitative yield). 1H NMR (400 MHz, CDCl3) : delta (ppm) = 7.77 (1H, d, J = 8.2 Hz), 7.69 (1H, d, J = 7.8 Hz), 7.40-7.29 (3H, m), 7.25-7.19 (2H, m), 4.69 (2H, s), 3.70 (2H, t, J = 5.3 Hz), 2.90 (2H, t, J = 5.7 Hz), 1.50 (9H, s).

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; Daiichi Sankyo Company, Limited; EP2256105; (2010); A1;,
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941294-25-3,941294-25-3, 1,3-Dichloro-7-fluoroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Compound 210C (3.0 g, 14 mmol) in acetic acid (10 mL) was added 55% aqueous HI solution (5 mL) and stirred at 100 C for 16 hours. The mixture was concentrated under reduced pressure. The residue was diluted with saturated NaHCCh solution (100 mL), extracted with ethyl acetate (50 mL x 3), washed with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to afford Compound 210D. LC-MS (ESI) m/z: 182 [M+H]+; 1H-NMR (CDCh, 400 MHz): d (ppm) 7.52-7.55 (m, 1H), 7.58-7.61 (m, 1H), 7.75 (s, 1H), 7.78-7.82 (m, 1H), 9.05 (s, 1H).

As the paragraph descriping shows that 941294-25-3 is playing an increasingly important role.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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6624-49-3, Isoquinoline-3-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,6624-49-3

General procedure: At 0 ¡ãC and with stirring to the solution of 865 mg (5.0 mmol) of isoquinoline-3-carboxylic acid in 10 ml of anhydrous THF 675 mg (5.0 mmol) of HOBt was added to form reaction mixture A. The solution of 5.5 mmol of l-amino acid benzylester in 5 ml of anhydrous THF was adjusted pH 9 with triethylamine and stirred for 30 min to form mixture B. At 0 ¡ãC the mixtures A and B were mixed and then 1339 mg (6.5 mmol) of DCC was added. The reaction mixture was stirred at 0 ¡ãC for 2 h, at room temperature for12 h and TLC (ethyl acetate/petroleum ether, 1:2) indicated the complete disappearance of isoquinoline-3-carboxylic acid. The formed precipitates of DCU were removed by filtration and the filtrate was evaporated under vacumm. The residue was dissolved in 50 ml of ethyl acetate and the formed solution was washed successively with saturated aqueous solution of NaHCO3 (30 ml .x. 3), 5percent aqueous solution of KHSO4 (30 ml .x. 3) and saturated aqueous solution of NaCl (30 ml .x. 3) and dried over anhydrous Na2SO4. After filtration the filtrate was evaporated under vacumm and the residure was purified on silica gel chromatography (CHCl3:MeOH, 20:1) to give the title compounds.

The synthetic route of 6624-49-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zheng, Meiqing; Yang, Yifan; Zhao, Ming; Zhang, Xiaoyi; Wu, Jianhui; Chen, Gong; Peng, Li; Wang, Yuji; Peng, Shiqi; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1672 – 1681;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.190777-77-6,5-Bromoisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

-1. 5-Bromo-2-methyl-2H-isoquinolin-l-one. [00116] To a mixture of 5-bromo-2H-isoquinolin-l-one (Preparation 4-1, 615 mg, 2.75 mmol) and cesium carbonate (1.79 g, 5.50 mmol) in NN-dimethylformamide (4.5 mL) and acetonitrile (1 1 mL) was added methyl iodid, 190777-77-6

The synthetic route of 190777-77-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; OBSCHESTVO S OGRANICHENNOY OTVETSTVENNOST’YU “PANACELA LABS”; GUROVA, Katerina; RYDKINA, Elena; WADE, Varren; WO2015/20553; (2015); 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

Isoquinolinone 4 was prepared from compound 1 through a 3-step sequence. Compound 1 was prepared using Method I and was then converted to 2 by coupling with A-2 according to Method L. Compound 2 was converted to compound 3 according to Method M. Method L[00407] An (S)-3-(l -Aminoethyl)-isoquinolin-l(2H)-one (1-5) (115 mmol, 1.0 eq), Cl-Wd (173 mmol, 1.5 eq) and triethylamine (344 mmol, 3.0 eq) are dissolved in n-BuOH (350 mL) and the mixture is stirred at reflux for 16 h. The reaction mixture is cooled to RT and concentrated in vacuo. The residue is slurried in a mixture of H20 (200 mL) and ethyl acetate (100 mL) and stirred at RT for 30 min. The solid is then collected by filtration, rinsed with ethyl acetate (25 mL) and dried in vacuo to afford the product (L-1).[00408] General method for the elaboration of Wd heterocycles:, 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; INTELLIKINE, INC.; INFINITY PHARMACEUTICALS, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2011/146882; (2011); A1;,
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Isoquinoline | C9H7N – PubChem

34784-07-1, 8-Chloroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: 8-chloro-5-nitroisoquinolineTo a solution of 8-chloroisoquinoline (1 mmol) in concentrated sulfuric acid at 0 0C was added potassium nitrate (1.1 mmol) .The reaction mixture was warmed to room temperature and stirred at room temperature for 5 hours. The reaction mixture was basified .Solid precipitated was column purified to afford a pale yellow solid.1H NMR (DMSO- d6): delta /77.76 – 7.79 ( IH, d , J = 8.4 Hz ); 8.48 – 8.51 ( IH, d , J = 8.4 Hz ); 8.53 – 8.55 ( IH, d , J = 6 Hz ); 8.86 – 8.88 ( IH, d , J = 6.3 Hz ); 9.84 ( IH , s )

34784-07-1, As the paragraph descriping shows that 34784-07-1 is playing an increasingly important role.

Reference£º
Patent; GLENMARK PHARMACEUTICALS S.A.; WO2007/42906; (2007); 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.34784-07-1,8-Chloroisoquinoline,as a common compound, the synthetic route is as follows.

20a) 1, 8-DICHLORO-ISOQUINOLINE To a solution of 8-chloro-isoquinoline (J. Org. Chem. 1977,42 (19), 3208-9.) (11 G, 54 MMOL) in CH2CI2 (200 mL) is added MCPBA (25 g, 112 MMOL) in several portions. After stirring for 3 hours, ether (400 mL) is added, followed by addition of hexanes (1 L). Solution stirred overnight and conc in vacuo, ether (200 mL) and hexanes (400 mL) is added, stirred overnight. The ppt is filtered, air dried and mixed with 20 g of POS and toluene (150 mL). The solution is heated to reflux for 3 h, neutralized with NAHCO3. Extracted the solution with CH2CI2. Organic layer then dried with sodium sulfate and conc in vacuo, yield 8 g (72%) of 1, 8-Dichloro-isoquinoline. MS: 198

34784-07-1, The synthetic route of 34784-07-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/28444; (2005); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1082674-24-5,6-Bromoisoquinoline-1-carbonitrile,as a common compound, the synthetic route is as follows.

Pd2dba3 (0.094 g, 0.10 mmol), BINAP (0.19 g, 0.31 mmol) and CS2CO3 (3.3 g, 10.3 mmol) were added to a degassed solution of 6-bromoisoquinoline-1 -carbonitrile (0.8 g, 3.4 mmol) in toluene (10 mL) followed by the addition of B5 (0.52 g, 3.8 mmol) under nitrogen atmosphere. The resulting reaction mixture was irradiated in a microwave at 1 10 C for 20 minutes. The reaction mixture was cooled to room temperature, diluted with EtOAc, filtered and the filtrate was washed with water. The organic layer was separated and the aqueous layer was extracted with EtOAc. The organic layers were combined, dried over Na2S04 and evaporated under reduced pressure to afford the crude mixture which was chromatographed on silica gel (100 – 200 mesh) using 25% EtOAc in petroleum ether to give B6 as a light brown solid (0.25 g, 25%). Rf: 0.4 (25% EtOAc/petroleum ether). Racemic: LCMS m/z = 288.1 (M + H). 1H NMR (300 MHz, CDCI3): delta 1.41 (d, J = 6.3 Hz, 3H), 2.27 – 2.38 (m, 1 H), 2.71 – 2.79 (m, 1 H), 3.30 – 3.38 (m, 1 H), 3.50 – 3.58 (m, 1 H), 4.38 – 4.44 (m, 1 H), 7.67 (d, J = 2.1 Hz, 1 H), 7.71 (dd, J = 2.1 , 9.3 Hz, 1 H), 7.83 (d, J = 5.7 Hz, 1 H), 8.35 (d, J = 9 Hz, 1 H), 8.61 (d, J = 5.7 Hz, 1 H). The racemic compound was chromatographed for enantiomeric separation. Conditions: Column: CHIRAL PAK IA, 4.6 X 250mm, 5 muGammaeta; Column ID: ANL_CHIR IA_145; Mobile Phase: A = hexane, B = isopropyl alcohol; ISOCRATIC: 60:40; FLOW: 0.8 mL/min; Column Temp: 25C; Eluent: EtOH Enantiomer of 8: Chiral HPLC purity: 99.38 % (retention time 12.55 minutes) LCMS m/z = 287.9 (M + H). 1 H NMR (300 MHz, cf6-DMSO): delta 1.30 (d, J = 6.3 Hz, 3H), 2.10 – 2.17 (m, 1 H), 2.65 – 2.76 (m, 1 H), 3.51 – 3.55 (m, 1 H), 3.70 – 3.79 (m, 1 H), 4.50 – 4.57 (m, 1 H), 7.81 (d, J = 2.1 Hz, 1 H), 7.87 (dd, J = 2.7, 9.0 Hz, 1 H), 8.20 (d, J = 5.4 Hz, 1 H), 8.28 (d, J = 9.0 Hz, 1 H), 8.64 (d, J = 5.7 Hz, 1 H)., 1082674-24-5

1082674-24-5 6-Bromoisoquinoline-1-carbonitrile 77174826, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER INC.; CHEKLER, Eugene Lvovich Piatnitski; GILBERT, Adam Matthew; UNWALLA, Rayomand Jal; VERHOEST, Patrick Robert; ANDERSON, James Thomas; WO2015/181676; (2015); A1;,
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