Electric Literature of 334952-09-9, These common heterocyclic compound, 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Electric Literature of 334952-09-9, These common heterocyclic compound, 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 8 N-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxoindoline-6-carboxamide Procedure: A mixture of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (82 mg, 0.2 mmol), 2-oxoindoline-6-carboxylic acid (36 mg, 0.2 mmol), EDCI (76 mg, 0.4 mmol) and N-methylimidazole (50 mg, 0.6 mmol) in 5 mL of DCM was stirred at room temperature for 16 hours. The mixture was washed with water (4 mL), The organic layer was dried over Na2SO4. After filtration and concentration, the residue was purified by preparative TLC (Silica gel, 20 cm*20 cm, separated by EtOAc, eluted by DCM_MeOH=1:20, v/v) to give N-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxoindoline-6-carboxamide (25 mg, 23.5%). 1H NMR (300 MHz, DMSO): delta 10.52 (s, 1H), 9.56 (s, 1H), 8.81 (s, 1H), 8.61 (d, 1H, J=6.3 Hz), 7.90 (brs, 1H), 7.48-7.46 (m, 2H), 7.28-7.25 (m, 2H), 6.93-6.90 (m, 1H), 4.54 (brs, 1H), 3.77-3.34 (m, 11H), 2.50-2.34 (m, 1H), 2.07-1.99 (m, 2H). LC-MS: 532 [M+H]+, 530 [M-H]-, tR=1.35 min. HPLC: 97.39% at 214 nm, 97.05% at 254 nm, tR=4.54 min.
Statistics shows that 2-Oxoindoline-6-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 334952-09-9.
Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem