Analyzing the synthesis route of 25475-67-6

25475-67-6, 25475-67-6 Isoquinolin-3-amine 311869, aisoquinoline compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25475-67-6,Isoquinolin-3-amine,as a common compound, the synthetic route is as follows.

[0553] Compound 516A was prepared from 473A by an analogous method as that of 473B, except using 3-aminoisoquinoline in place of 2-bromo-6-aminopyridine.

25475-67-6, 25475-67-6 Isoquinolin-3-amine 311869, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Das, Jagabandhu; Padmanabha, Ramesh; Chen, Ping; Norris, Derek J.; Doweyko, Arthur M.P.; Barrish, Joel C.; Wityak, John; Lombardo, Louis J.; Lee, Francis Y.F.; US2004/54186; (2004); A1;,
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Downstream synthetic route of 552331-05-2

As the paragraph descriping shows that 552331-05-2 is playing an increasingly important role.

552331-05-2,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.552331-05-2,6-Bromo-1,3-dichloroisoquinoline,as a common compound, the synthetic route is as follows.

Example 80C 6-Bromo-3-chloro-isoquinoline A mixture of Example 80B (1.8 g, 6.5 mmol), P (0.48 g, 15.5 mmol) and HI (3 ml, 48%) in acetic acid (20 ml) was refluxed for 8 hours, filtrated under hot condition and concentrated under vacumm. The residue was basified by adding sodium hydroxide solution, treated with ethyl acetate (200 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexane to provide the title compound (0.81 g, 50%). MS (DCI/NH3) m/e 244 (M+H)+.

As the paragraph descriping shows that 552331-05-2 is playing an increasingly important role.

Reference£º
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); A1;,
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Downstream synthetic route of 1350643-72-9

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

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

4 mg (0.013 mmol) of 4-chloro-6-fluoro-8-(4-methoxybenzyl)pyrido[2,3-d]pyrimidine-5(8H)-one prepared in step 5 and 4 mg (0.014 mmol) of (S)-3-(1-aminoethyl)-8-chloro-2-phenylisoquinoline-1(2H)-one were dissolved in 1 mL of anhydrous dimethylsulfoxide (DMSO), to which 6.6 muL (0.039 mmol) of diisopropylethylamine (DIPEA) was added, followed by stirring at 70 C. for 5 hours. The reaction mixture was cooled down to room temperature. Ethyl acetate and water were added thereto, followed by extraction. The extracted organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was separated by column chromatography (SiO2, eluent: hexane/ethyl acetate, 4/1->hexane/ethyl acetate, 1/1) to give 6 mg of the target compound (S)-4-((1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinoline-3-yl)ethyl)amino)-6-fluoro-8-(4-methoxybenzyl)pyrido[2,3-d]pyrimidine-5(8H)-one as a pale yellow solid (0.010 mmol, yield: 82%). 1H NMR (300 MHz, CDCl3) delta 10.53 (d, J=6.6 Hz, 1H), 8.31 (s, 1H), 7.61 (d, J=6.9 Hz, 1H), 7.47-7.57 (m, 2H), 7.30-7.47 (m, 6H), 7.22 (d, J=8.2 Hz, 2H), 7.88 (d, J=8.2 Hz, 2H), 6.58 (s, 1H), 5.38 (s, 2H), 4.95 (q, J=4.2 Hz, 5.2 Hz, 1H), 3.79 (s, 3H), 1.46 (d, J=6.9 Hz, 3H)., 1350643-72-9

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

Reference£º
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Lee, Ge Hyeong; Lim, Hee-Jong; Cho, Heeyeong; Park, Woo Kyu; Kim, Seong Hwan; Choi, Jung Hwan; (148 pag.)US2018/105527; (2018); A1;,
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Brief introduction of 552331-06-3

The synthetic route of 552331-06-3 has been constantly updated, and we look forward to future research findings.

552331-06-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.552331-06-3,6-Bromo-3-chloroisoquinoline,as a common compound, the synthetic route is as follows.

A solution of 6-bromo-3-chloro-isoquinoline (8.0 g, 33 mmol) and tributyl-(1 -ethoxyvinyl)- tin (14.88 g, 14 ml_, 41 .2 mmol) in toluene (100 ml.) was degassed with nitrogen for 30 min. Bis(triphenylphosphine)palladium(ll) dichloride (1.16 g, 1 .65 mmol, 5 mol%) was added and the reaction mixture was heated at 60C for 20 h. The reaction mixture was cooled to RT, the mixture was filtered and the filtrate was evaporated. The residue was purified by silica gel chromatography using a gradient of /’so-hexanes/ethyl acetate 20:1 to 10:1 to afford the title compound (7.1 g, 92%) as a yellow solid

The synthetic route of 552331-06-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GILEAD SCIENCES, INC.; SELCIA LIMITED; ACIRO, Caroline; STEADMAN, Victoria Alexandra; PETTIT, Simon Neil; POULLENNEC, Karine G.; LAZARIDES, Linos; DEAN, David Kenneth; DUNBAR, Neil Andrew; HIGHTON, Adrian John; KEATS, Andrew John; SIEGEL, Dustin Scott; KARKI, Kapil Kumar; SCHRIER, Adam James; JANSA, Petr; MACKMAN, Richard; WO2013/185103; (2013); A1;,
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Some tips on 164148-92-9

164148-92-9, The synthetic route of 164148-92-9 has been constantly updated, and we look forward to future research findings.

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

At room temperature,6-amino-3,4-dihydroisoquinolin-2 (1H) -carboxylic acid, t-butyl ester (500 mg)Triethylamine (0.337 mL)And THF (10 mL)Was added 2,2,2-trichloroethyl chloroformate (0.333 mL)The resulting mixture was stirred in a nitrogen atmosphere,Stir at the same temperature for 10 minutes.At room temperature, water was added to the reaction mixture,And the aqueous layer was extracted with ethyl acetate.The extract was washed with water and brine and dried over anhydrous magnesium sulfate,And the solvent was removed by distillation under reduced pressure.A solution of 4M hydrochloric acid in ethyl acetate (5 mL) was added to a mixture of the residue and ethyl acetate (5 mL) at room temperature, and the resulting mixture was stirred under nitrogen atmosphere for 3 days.The precipitate was collected by filtration and washed with ethyl acetate to give the title compound (652 mg).

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; TAKEDA PHARMACEUTICAL COMPANYLIMITED; HIRAYAMA, TAKAHARU; FUJIMOTO, JUN; CARY, DOUGLAS ROBERT; OKANIWA, MASANORI; HIRATA, YASUHIRO; (289 pag.)TW2017/14883; (2017); A;,
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New learning discoveries about 660830-62-6

As the paragraph descriping shows that 660830-62-6 is playing an increasingly important role.

660830-62-6, Ethyl 7-bromoisoquinoline-3-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,660830-62-6

To a solution of ethyl 7-bromoisoquinoline-3-carboxylate (0.46 g, 1.6 mmol) in dichloromethane (10 mL) at 0 C was added 3-chlorobenzoperoxoic acid (0.55 g, 2.4 mmol) in one portion. The resulting solution was stirred at room temperature for 22 h, quenched with saturated aqueous NaHCO3 (20 mL) and extracted with dichloromethane (3 x 40 mL). The combined extracts were dried over Na2504, filtered and concentrated in vacuo todryness. The residue was loaded onto an Isco solid load cartridge and purified by flash chromatography on Si02 (60-95% EtOAc/hexanes) to give 7-bromo-3- (ethoxycarbonyl)isoquinoline 2-oxide (0.34 g, 1.1 mmol, 70% yield) as a white solid. MS (ESI) m/z: 297.9 (M+H).

As the paragraph descriping shows that 660830-62-6 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; CARPENTER, Joseph E.; BROEKEMA, Matthias; FENG, Jianxin; LIU, Chunjian C.; WANG, Wei; WANG, Ying; (244 pag.)WO2019/89670; (2019); A1;,
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Downstream synthetic route of 19493-45-9

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19493-45-9,3-Chloroisoquinoline,as a common compound, the synthetic route is as follows.

Compound A1 (5 mmol) and compound B5 (6 mmol) were weighed into a three-necked flask, Pd(pph3)4 (0.15 mmol) was added as a catalyst, and K2CO3 (16 mmol) was added.In a double-row tube, vacuum-nitrogen gas-vacuum was evacuated and the cycle was repeated three times. Finally, the reaction system was protected with nitrogen gas.Add 15 mL each of dimethyl ether and water with a syringe and heat to reflux.The reaction was refluxed for 24 h and cooled to room temperature. After vortexing, the column was purified to give the product 51.

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

Reference£º
Patent; Shanghai Hehui Optoelectric Co., Ltd.; Liang Hua; (13 pag.)CN107586308; (2018); A;,
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Brief introduction of 215453-51-3

As the paragraph descriping shows that 215453-51-3 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.215453-51-3,7-Bromo-1-chloroisoquinoline,as a common compound, the synthetic route is as follows.

215453-51-3, To a solution of compound 1.5 (3 g, 12.4 mmol, 1 eq) in NMP (30 mL) was addedNH.HzO (30 mL). The mixture was stirred 150C for 15 hours. The reaction mixture wasquenched by addition H20 100 mL at 25 C, and then extracted with EtOAC (100 mL x 3). The combined organic layers were washed with saturated brines (15 mL x 1), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a crude product. The residue was purified by column chromatography (Si02, Petroleum ether/Ethylacetate=1:1). Compound 1.4 (2.0 g, 9 mmol, 72.42% yield) was obtained as a brown oil. LCMS (ESI): m/z: [M + H] calcd for C9H7N2Br:223; found 223; RT=1.049 mm.

As the paragraph descriping shows that 215453-51-3 is playing an increasingly important role.

Reference£º
Patent; CORTEXYME, INC.; LYNCH, Casey C.; KONRADI, Andrei; GALEMMO, JR., Robert A.; (218 pag.)WO2018/209132; (2018); A1;,
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Downstream synthetic route of 63927-23-1

As the paragraph descriping shows that 63927-23-1 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.63927-23-1,5-Bromo-8-nitroisoquinoline,as a common compound, the synthetic route is as follows.

63927-23-1, EXAMPLE 26 5-Bromo-2-ethyl-1,2,3,4-tetrahydro-8-nitroisoquinoline A solution of 5-bromo-8-nitroisoquinoline (1 g, 3.95 mmol) in 20 mL THF was cooled to 0 C. and treated sequentially with sodium borohydride (0.75 g, 19.83 mmol) followed by the slow addition of acetic acid (20 mL). The reaction mixture was allowed to warm to room temperature, and an additional 2 equiv. of sodium borohydride was added. After quenching with water and treatment with sodium hydroxide solution to make basic, the reaction mixture was extracted with ethyl acetate. The organic residue was chromatographed on silica gel (25% ethyl acetate in hexane) to give the N-ethyl-5-bromo-8-nitrotetrahydroisoquinoline (0.8 g, 70% yield).

As the paragraph descriping shows that 63927-23-1 is playing an increasingly important role.

Reference£º
Patent; BIGGE, CHRISTOPHER F.; MALONE, THOMAS C.; WATJEN, FRANK; US2003/114422; (2003); A1;,
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Brief introduction of 23687-25-4

As the paragraph descriping shows that 23687-25-4 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23687-25-4,Isoquinolin-4-amine,as a common compound, the synthetic route is as follows.,23687-25-4

To a stirring solution of 4-aminoisoquinoline (1.4 g, 10.0 mmol) in 5 N aqueous hydrochloric acid (12 mE) at 00 C. was added a solution of sodium nitrite (NaNO2, 0.069 g, 10.0 mmol) in deionized water (1 mE), while maintaining the internal temperature below 00 C. The reaction mixture was stirred at 00 C. for 30 mm and a solution of tin(II) chloride dihydrate (SnC12.2H20, 5.6 g, 25.0 mmol) dissolved in concentrated hydrochloric acid (5 mE) was added dropwise. The mixture was stirred at room temperature for 2 h and the solution was adjusted to pH -12-14 with 20% aqueous sodium hydroxide. The mixture was extracted with 2:1 CHC13/iPrOH. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude product was purified by flash chromatography (Si02, 50% ethyl acetate in hexanes) to give the desired compound (0.84 g, 5.3 mmol, 53%)

As the paragraph descriping shows that 23687-25-4 is playing an increasingly important role.

Reference£º
Patent; ChemoCentryx, Inc.; Cappel, Markus; (83 pag.)US2018/9797; (2018); A1;,
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