Category: isoquinoline

19493-45-9, 3-Chloroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 23 :3-(piperazin-l-yl)isoquinoline[00436] A mixture of 3-chloroisoquinoline (200 mg, 1.22 mmol) and piperazine (2.10 g, 24.4 mmol) in ethylene glycol (2 ml) was heated to 150C and stirred at that temperature for 24 hours. The reaction was allowed to cool down to room temperature. The crude mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated under vacuo. The residue was and purified on silica gel by flash column chromatography to give the title compound as a pale brown solid (131 mg, 50% yield).[00437 ] 1H NMR (CDCl3, 400 MHz) delta 3.18 (4H, t), 3.67 (4H, t), 6.81 (IH, s), 7.31 (IH, t), 7.54 (1 H, t), 7.62 (IH, d), 7.82 (IH, d), 8.97 (IH, s); MS (ES+) 214.

19493-45-9 3-Chloroisoquinoline 640968, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/94992; (2008); A2;,
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891785-28-7, 6-Bromoisoquinolin-3-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3 A mixture of DIPEA (5.86 mL, 33.62 mmol), DMAP (0.27 g, 2.24 mmol) and HATU (5.11 g, 13.45 mmol) in DMF (30 mL) was stirred for 10 min. 6-Bromoisoquinolin-3-amine (XII) (2.5 g, 11.21 mmol) was then added followed by the addition of trans-4-[[tert-butyl (dimethyl)silyl]oxymethyl]cyclohexanecarboxylic acid (LIII) (3.66 g, 13.45 mmol). The mixture was heated to 70 C. overnight. An additional 0.5 equiv. of HATU were added and the mixture was continued for additional 6 h. The solvent was concentrated, the residue taken up in EtOAc, washed with sat. NaHCO3 and brine. The organic layer was then concentrated and the crude product was purified by column chromatography (0?30% EtOAc/hexanes). The pure fractions were combine and concentrated to obtain trans-N-(6-bromo-3-isoquinolyl)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclohexanecarboxamide (LIV) (2.25 g, 4.71 mmol, 42.0% yield) as a crystalline off-white solid. 1H NMR (499 MHz, DMSO-d6) delta ppm 0.03 (6H, s), 0.87 (9H, s), 0.98 (2H, qd, J=12.72, 3.29 Hz), 1.38-1.51 (3H, m), 1.73-1.82 (2H, m), 1.85-1.92 (2H, m), 2.46-2.55 (1H, m), 3.41 (2H, d, J=6.04 Hz), 7.62 (1H, dd, J=8.64, 1.78 Hz), 7.99 (1H, d, J=8.78 Hz), 8.16 (1H, d, J=1.65 Hz), 8.44 (1H, s), 9.13 (1H, s), 10.53 (1H, s); ESIMS found for C23H33BrN2O2Si m/z 477.2 (79BrM+1).

As the paragraph descriping shows that 891785-28-7 is playing an increasingly important role.

Reference£º
Patent; Samumed, LLC; KC, Sunil Kumar; Mittapalli, Gopi Kumar; Hofilena, Brian Joseph; Marakovits, Joseph Timothy; Chiruta, Chandramouli; Mak, Chi Ching; Cao, Jianguo; (324 pag.)US2017/313681; (2017); A1;,
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69454-42-8, Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of methyl 4-chloroisoquinoline-2-carboxylate: Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate (0.68g, 3.3mmoles) was dissolved in excess phosphorus oxy chloride (5 mis) and the clear solution heated (950C) for 3 hours and overnight at room temperature. The reaction was diluted with toluene (10mIs) and azeotroped twice. The residual oil was diluted with dichloromethane (10mls) and quenched with ice cooled water (50mIs). Further dichloromethane was added (15mls) and the layers separated. The aqueous layer was extracted with dichloromethane (10mIs) and the dichloromethane phases combined and washed with saturated sodium bicarbonate (10mIs), water (10mIs) and brine (10mIs). After drying over magnesium sulphate the solution was filtered and concentrated to give an off white solid. (0.47g, 64% yield).

69454-42-8 Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate 641183, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; QUEEN MARY AND WESTFIELD COLLEGE; COTTER, Finbarr, Edward; WO2010/125343; (2010); A1;,
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18881-17-9, (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: {(3S)-2-[(4-Methylphenyl)sulphonyl]-1,2,3,4-tetrahydroisoquinolin-3-yl}methyl 4-methylbenzenesulphonate To a solution of 30.2 g of [(3S)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol (185 mmol) in 750 mL of dichloromethane there are successively added 91.71 g of tosyl chloride (481 mmol) and then, dropwise, 122.3 mL of N,N,N-triethylamine (740 mmol). The reaction mixture is then stirred at ambient temperature for 20 hours. It is then diluted with dichloromethane, washed successively with 1M HCl solution, saturated aqueous NaHCO3 solution and then brine until neutral. The organic phase is then dried over MgSO4, filtered and concentrated to dryness. The solid obtained is then dissolved in a minimum volume of dichloromethane and then cyclohexane is added until a precipitate is formed. This precipitate is then filtered off and washed with cyclohexane. After drying, the title product is obtained in the form of crystals. 1H NMR: delta (400 MHz; dmso-d6; 300 K): 7.75 (d, 2H, aromatic Hs, ortho O-tosyl); 7.6 (d, 2H, aromatic Hs, ortho N-tosyl); 7.5 (d, 2H, aromatic Hs, meta O-tosyl); 7.3 (d, 2H, aromatic Hs, meta N-tosyl); 7.15-6.9 (m, 4H, aromatic Hs, tetrahydroisoquinoline); 4.4-4.15 (dd, 2H, aliphatic Hs, tetrahydroisoquinoline); 4.25 (m, 1H, aliphatic H, tetrahydroisoquinoline); 4.0-3.8 (2dd, 2H, aliphatic Hs, CH2-O-tosyl); 2.7 (2dd, 2H, aliphatic Hs, tetrahydroisoquinoline); 2.45 (s, 3H, O-SO2-Ph-CH3); 2.35 (s, 3H, N-SO2-Ph-CH3) IR: nu: -SO2: 1339-1165 cm-1

The synthetic route of 18881-17-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; US2015/31648; (2015); A1;,
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396-29-2, 3-Fluoroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 175A 3-fluoro-5-isoquinolinamine The title compound was prepared using the procedures described in Examples 60D and 60E using 3-fluoroisoquinoline, prepared according to the procedure described in J. Am. Chem. Soc., 687:73 (1951), instead of the product from Example 60C.

The synthetic route of 396-29-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Lee, Chih-Hung; Bayburt, Erol K.; DiDomenico JR., Stanley; Drizin, Irene; Gomtsyan, Arthur R.; Koenig, John R.; Perner, Richard J.; Schmidt JR., Robert G.; Turner, Sean C.; White, Tammie K.; Zheng, Guo Zhu; US2004/157849; (2004); A1;,
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90806-58-9, 5-Methoxyisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of Cap-138, step a (2.34 g, 14.7 mmol) in anhydrous dichloromethane (50 mL) at room temperature was added meto-chloroperbenzoic acid (77%, 3.42 g, 19.8 mmol) in one portion. After being stirred for 20 h, powdered potassium carbonate (2.0 g) was added and the mixture was stirred for 1 h at room temperature before it was filtered and concentrated to afford Cap-138, step b as a pale, yellow solid which was sufficiently pure to carry forward (2.15 g, 83.3%). 1H NMR (CDC13, 400 MHz) delta 8.73 (d, J= 1.5 Hz, 1H), 8.11 (dd, J = 7.3, 1.7 Hz, 1H), 8.04 (d,J=7.1 Hz, 1H), 7.52 (t, J= 8.1 Hz, 1H), 7.28 (d, J = 8.3 Hz, 1H), 6.91 (d, J= 7.8 Hz, 1H), 4.00 (s, 3H); Rt= 0.92 min, (Cond.-Dl); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C10H10N02: 176.07; found: 176.0.

As the paragraph descriping shows that 90806-58-9 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; PACK, Shawn, K.; TYMONKO, Steven; PATEL, Bharat, P.; NATALIE, JR., Kenneth, J.; BELEMA, Makonen; WO2011/59850; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.215453-26-2,6-Bromoisoquinolin-1-ylamine,as a common compound, the synthetic route is as follows.

Into a 250-mL round-bottom flask, was added 6-bromoisoquinolin-1-amine (500 mg, 2.24 mmol), NCS (359 mg, 2.69 mmol) and chloroform (50 mL). The reaction mixture was stirred for 24 h at 60 C. in an oil bath. The solution was diluted with 50 mL of water and extracted with 2*50 mL of dichloromethane. The organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography with methanol:dichloromethane (3:10). This resulted in 400 mg (69%) of 6-bromo-4-chloroisoquinolin-1-amine as a purple solid. [M+H]+ 356/358. Rt 1.12 min (method R).

The synthetic route of 215453-26-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck Patent GmbH; Cancer Research Technology, Ltd.; SCHIEMANN, Kai; BLAGG, Julian; MALLINGER, Aurelie; RINK, Christian; SEJBERG, Jimmy; HONEY, Mark; (139 pag.)US2016/16951; (2016); A1;,
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3336-43-4, 1-Chloroisoquinolin-4-ol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 34:3-Amino-l-(3-bromo-4,5-dimethoxy-phenyl)-9-chloro-lH-4-oxa-10-aza-phenanthrene-2- carbonitrile (34)(34)l-Chloro-4-hydroxyisoquinone (790 mg, 4.4 mmol), 5-bromo-3,4-dimethoxy-benzaldehyde ( 1.077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 mu, 1.46 mmol) and then stirred at 80 C under LC-MS control for 24 h. The reaction mixture was cooled down to room temperature, diluted with water to about 100 ml and the precipitates were collected by filtration, washed well with 50 % aqueous ethanol and dried under vacuum to yield the title compound (1.7 g, 3.6 mmol, 82 %).

3336-43-4 1-Chloroisoquinolin-4-ol 4281882, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; Deutsches Krebsforschungszentrum (DKFZ); Ruprechts-Karls-Universitaet Heidelberg; BOUTROS, Michael; MASKEY, Rajendra-Prasad; KOCH, Corinna; FUCHS, Florian; STEINBRINK, Sandra; GILBERT, Daniel; WO2012/62901; (2012); A2;,
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Isoquinoline | C9H7N – PubChem

82827-09-6, 6-Bromoisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Under nitrogen atmosphere, 22 mg of 60% sodium hydride was added at 0C to 3 ml solution of dimethylformamide with 100 mg of 6-bromo-2H-isoquinoline-1-one, and the mixture was stirred for 30 min. 0.04 ml of ethyl iodide was added at 0C, and the mixture was stirred at room temperature for 3 hours. Cold water was added to the reaction solution, extracted with chloroform. Chloroform layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by thin-layer chromatography (hexane/ethyl acetate=3/1) to obtain 30 mg of the above compound as a white solid. 1HNMR(400MHz,CDCl3.)delta.:1.38(3H,t,J=7.4Hz), 4.04(2H,q,J=7.2Hz), 6.41(1H,d,J=7.2Hz), 7.10(1H,d,J=7.6Hz), 7.56(1H,dd,J=1.8,8.6Hz), 7.67(1H,d,J=2.0Hz), 8.28(1H,d,J=8.4Hz) ESI-MS Found:m/z 253.9[M+H]+

The synthetic route of 82827-09-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1726585; (2006); 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.216064-48-1,tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.

In aN2 blanketed flask, 19.7 g (79.0 mmol) of 5-hydroxy-3,4-dihydro-lH-isoquinoline-2-carboxylic acid tert-butyl ester is dissolved in 300 mL of DMF, and.4.1g(79.2 mmol) of N-bromosuccihimide is added in one portion. The solution is stirredovernight and quenched with 500 mL of HaO. The resulting mixture is partitionedbetween 500 mL of EtOAc and 500 mL of H^O. The aqueous layer is extracted twicewith 400 mL of EtOAc, and the combined organic layer is washed with 300 mL of brineand dried over Na2SO4. Solvent is removed to afford 39.8 g crude product includingresidual DMF. The crude 8-bromo-5-hydroxy-3,4-dihydro-lH-isoquinoline-2-carboxylicacid tert-butyl ester is dissolved in 390 mL of acetone, and then 12.5 g (90.4 mmol) ofK^COs is added followed by 10.3 mL (14.8 g, 86.6 mmol) of benzyl bromide. Themixture is stirred at reflux 20h, and then cooled to ambient temperature and filtered. Thefiltrate is evaporated, and the residue is partitioned between 50 mL of H^O and 100 mL ofEtOAc. The aqueous layer is extracted with EtOAc (2 X 100 mL). The combinedorganic layer is washed with brine and dried over Na2SO4. The solvent is removed toafford crude product as an orange-brown oil which is purified by silica gelchromatography to afford clean product of 8-bromo-5-benzyloxy-3,4-dihydro-lH-isoquinoline-2-carboxylic acid tert-butyl ester as 34.1 g of orange oil which crystallizedupon standing. 1H NMR (250 MHz, CDC13) 8 7.3-7.15 (6H, m), 6.56 (1H, d, J=7.5 Hz),4.94 (2H, s), 4.42 (2H, s), 3.53 (2H, t, J=5.7 Hz), 2.71 (2H, d, J=5.7 Hz), 1.42 (9H, s).

216064-48-1 tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 10538586, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/51945; (2005); A1;,
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