Analyzing the synthesis route of 6624-49-3

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

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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Simple exploration of 6624-49-3

Big data shows that 6624-49-3 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.6624-49-3,Isoquinoline-3-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: To the resin 13 (560 mg) in DMF (2.5 mL) were added a solutionof the appropriate Fmoc-protected amino acid (see Tables 1?3)(0.3 M), PyBOP (0.3 M) and HOBt (0.3 M) in dry DMF (4.2 mL). Thesuspensions were stirred for 3 min and then DIPEA (0.6 M) wasadded. The suspensions were stirred for 3 h under an argon atmosphereat rt. The resins were washed successively with DCM(150 mL), MeOH (120 mL), DCM (75 mL) and dried overnight undervacuum to give resins 14, each bearing an appropriate Fmoc-protectedamino acid. To the resins 14 (161 mg, 0.13 mmol) wereadded a solution of piperidine (20percent, v/v) in DCM (2.1 mL) and themixtures were stirred for 1 h at rt. After filtration, the resins werewashed successively with DCM (50 mL), MeOH (45 mL), DCM(25 mL) and dried under vacuum to give resins 15. Portions(65 mg) of resins 15 were placed in reactor wells (12 mL) of anautomated synthesizer reaction block (40-well format) (AdvancedChemTech). To each well was added a solution of appropriate carboxylicacid (see Tables 1?3) (0.3 M), PyBOP (0.3 M) and HOBt 6-Cl(0.3 M) and DIPEA (0.6 M) in dry DMF (2 mL). The suspensionswere vortexed at 300 rpm over a period of 5 h under an argonatmosphere. The wells were then filtered to remove the reactivesolution from the resins 16 and washed successively with THF,DCM, MeOH and DCM., 6624-49-3

Big data shows that 6624-49-3 is playing an increasingly important role.

Reference£º
Article; Talbot, Amelie; Maltais, Rene; Kenmogne, Lucie Carolle; Roy, Jenny; Poirier, Donald; Steroids; vol. 107; (2016); p. 55 – 64;,
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Downstream synthetic route of 6624-49-3

As the paragraph descriping shows that 6624-49-3 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.6624-49-3,Isoquinoline-3-carboxylic acid,as a common compound, the synthetic route is as follows.

6624-49-3, A solution of 2 (519.0 mg, 3.0 mmol) and mono-N-Boc-protected TREN (3) (246.0 mg, 1.0 mmol) in DMF (50 mL) was prepared at room temperature under nitrogen. While stirring, DMTMM (4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholiniumchloride) (830.1 mg, 3 mmol) and NMM (N-methylmorpholine) were added (dropwise 2-3 ml) to get a pH of about 9. Then solution was diluted with methanol (10 ml) and allowed to stir at room temperature. After 12 h, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate. After removal of solvent the crude product was purified by column chromatography using silica gel and CH2Cl2:MeOH (20:1). The product 4 (338.6 mg, 61%) was obtained as a white solid.

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Reference£º
Article; Gao, Fei; Liu, Haiqing; Li, Li; Guo, Jianpeng; Wang, Yuji; Zhao, Ming; Peng, Shiqi; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4434 – 4436;,
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New learning discoveries about 6624-49-3

As the paragraph descriping shows that 6624-49-3 is playing an increasingly important role.

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.

As the paragraph descriping shows that 6624-49-3 is playing an increasingly important role.

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;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Some tips on 6624-49-3

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

6624-49-3, Isoquinoline-3-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The ligand (1 eq) and sodium methoxide (1.1 eq) were dissolved in dry methanol (10mL) and after stirring at room temperature for 15min, [RhCp*(mu-Cl)Cl]2 (0.9 eq) was added. The mixture was stirred under argon atmosphere and at room temperature for 24h. The solvent was subsequently removed under reduced pressure; the obtained residue was taken up in CH2Cl2 and filtered to remove insoluble reaction by-products. The filtrate was concentrated to a volume of 2mL under reduced pressure. Precipitation with n-hexane afforded the desired product in moderate to good yields (53?64percent)., 6624-49-3

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

Reference£º
Article; Doemoetoer, Orsolya; Hackl, Carmen M.; Bali, Krisztina; Roller, Alexander; Hejl, Michaela; Jakupec, Michael A.; Keppler, Bernhard K.; Kandioller, Wolfgang; Enyedy, Eva A.; Journal of Organometallic Chemistry; vol. 846; (2017); p. 287 – 295;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Downstream synthetic route of 6624-49-3

As the paragraph descriping shows that 6624-49-3 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.6624-49-3,Isoquinoline-3-carboxylic acid,as a common compound, the synthetic route is as follows.,6624-49-3

General procedure: Mixtures of 4-(di-tert-butoxycarbonylamino)-6-amino-2-methylquinoline (100mg, 0.27mmol), the respective carboxylic acid (0.53mmol, 2equiv), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU; 190mg, 0.500mmol, 2.0equiv) and di-iso-propylethylamine (0.5mL, 2.9mmol, 10equiv) in DMF (5mL) were stirred at room temperature for 16h. The mixtures were poured into 50mL of 5percent aq Na2CO3 and extracted with EtOAc (3¡Á50mL). The combined organic layers were washed with 5percent aq Na2CO3 (1¡Á50mL), brine (1¡Á50mL), dried (MgSO4), and evaporated. The residual materials were co-evaporated with diethyl ether and treated without further purification with 1:1 TFA/DCM (5mL) for 30min?2h. Removal of solvents gave crude materials as solids or oils that were triturated with diethyl ether and recrystallized from CH3CN/MeOH) to yield the final product as a TFA salt or purified using prep TLC (80:18:2 CHCl3/MeOH/aq CH3NH2) to provide the free base. Some of the free bases were further reacted with a slight excess of p-toluenesulfonic acid in diethyl ether to provide the corresponding p-TsOH salts.

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Reference£º
Article; Williams, John D.; Khan, Atiyya R.; Cardinale, Steven C.; Butler, Michelle M.; Bowlin, Terry L.; Peet, Norton P.; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 419 – 434;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Downstream synthetic route of 6624-49-3

As the paragraph descriping shows that 6624-49-3 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.6624-49-3,Isoquinoline-3-carboxylic acid,as a common compound, the synthetic route is as follows.

6624-49-3, General procedure: To a mixture of A-b (100 mg, 0.43 mmol), acid (0.51 mmol), HATU (241 mg, 0.64 mmol) and DIPEA (109 mg, 0.85 mmol) in DMF (3 mL) was stirred at 25 C for 16 h. The mixture was diluted by the addition of water (20 mL). General Work-up Procedure 1 was followed. The residue was purified by prep-HPLC or Chromatography to afford the title compound. Followed General procedure 3 to afford 8b (126 mg, 20%). MS (ESI) calc?d for (C2IH19N5OS) [M+Hf, 390.1; found, 390.0. NMR (300 MHz, DMSO-r/6) d 10.77 (s, 1H), 9.48 (s, 1H), 8.72 (s, 1H), 8.55 (s, 1H), 8.33 – 8.24 (m, 2H), 8.00 – 7.83 (m, 4H), 7.34 (t, J = 7.8 Hz, 1H), 7.04 (d, J = 7.8 Hz, 1H), 4.70 (q, .7 = 6.9 Hz, 1H), 3.42 (s, 3H), 1.69 (d, .7 = 6.9 Hz, 3H).

As the paragraph descriping shows that 6624-49-3 is playing an increasingly important role.

Reference£º
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
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Analyzing the synthesis route of 6624-49-3

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

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: Removal of the Boc protecting group of compound 5 was preformed at room temperature for 1 h with a solution of HCl 4N in dioxane. The mixture was then concentrated in vacuo, diluted with MeOH, and concentrated several times in vacuo. The residue was coupled with various carboxylic acids (1.1 equiv), in the presence of BOP (1.1 equiv) and DIEA (pH=9) for 2 h, in DCM. The mixture was then concentrated in vacuo, and the residue was dissolved in AcOEt. The organic layer was successively washed with aqueous solutions of 1M KHSO4, saturated NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to yield the desired compound. All the final compounds were purified by preparative HPLC on a C18 column using a water/acetonitrile/TFA 0.1percent gradient.

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

Reference£º
Article; Blayo, Anne-Laure; Maingot, Mathieu; Aicher, Babette; M’Kadmi, Cline; Schmidt, Peter; Mueller, Gilbert; Teifel, Michael; Guenther, Eckhard; Gagne, Didier; Denoyelle, Sverine; Martinez, Jean; Fehrentz, Jean-Alain; Bioorganic and Medicinal Chemistry Letters; vol. 25; 1; (2015); p. 20 – 24;,
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Simple exploration of 6624-49-3

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6624-49-3,Isoquinoline-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 71ISOQUINOLINE-3-CARBOXYLIC ACID [(R)-1-(2-FLUORO-4-METHANESULFONYLAMINO-5-METHYLPHENYL)ETHYL]AMIDE To a stirred solution of isoquinoline-3-carboxylic acid (26 mg, 0.15 mmol), N-[4-((R)-1-aminoethyl)-5-fluoro-2-methylphenyl]methanesulfonamide hydrochloride (35 mg, 0.12 mmol), and N,N,N’,N’-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (56 mg, 0.15 mmol) in N,N-dimethylformamide (0.5 g) was added N,N-diisopropylethylamine (80 mg, 0.62 mmol). A catalytic amount of DMAP was added and the reaction was stirred for 16 hours at room temperature. The reaction mixture was concentrated and purified by flash chromatography (0 to 5percent MeOH in CH2Cl2). The resulting product was shaken with water and extracted with EtOAc (3.x.). The combined organics were dried (MgSO4), filtered and concentrated to give the title compound (36.8 mg, 74percent) as a white solid. m/z=402.0 (M+1), r.t. 3.01 min. 1H NMR (400 MHz; d6-DMSO) 9.42 (1H, s), 9.21 (1H, s), 916 (1H, 8.53 (1H, s), 8.27 (1H, d), 8.19 (1H, d), 7.87 (1H, t), 7.84 (1H, t), 7.43 (1H d), 7.10 (1H, d), 5.49-5.40 (1H, m), 3.19 (3H, s), 2.23 (3H, s), 1.54 (3H, d)., 6624-49-3

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

Reference£º
Patent; PFIZER INC.; RENOVIS, INC.; US2012/88746; (2012); A1;,
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New learning discoveries about 6624-49-3

As the paragraph descriping shows that 6624-49-3 is playing an increasingly important role.

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, The compound 3-isoquinolinecarboxylic acid (0801-132) (1.0 g, 5.78 mmol, 1.0 eq.)Dissolved in 30 ml of methanol,Sulfuric acid (0.5 ml) was then added and the reaction was refluxed overnight.After the reaction is finished, add sodium bicarbonate solutionpH to 8, extracted with dichloromethane, liquid-separated, and the organic phase dried over anhydrous sodium sulfate.Spin-drying afforded the compound 3-isoquinolinecarboxylic acid methyl ester (810 mg, 75percent).

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Reference£º
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
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