Related Products of 23814-14-4,Some common heterocyclic compound, 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, molecular formula is C8H6N2O3, 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 14 N-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide Procedure: A mixture of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (100 mg, 0.245 mmol), 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid (48 mg, 0.27 mmol), EDCI (97 mg, 0.49 mmol) and N-methylimidazole (60 mg, 0.735 mmol) in 10 mL of DCM was stirred at room temperature for 16 hours. The mixture was washed with water (5 mL), The organic layer was dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography on silica gel eluting with a mixture of CH2Cl2 and methanol (100:1: to 20:1, V/V) to give N-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide (25 mg, 19%) as white solid. 1H NMR (300 MHz, DMSO): delta 9.57 (s, 1H), 8.81 (s, 1H), 8.475-8.46 (m, 1H), 8.27-8.25 (m, 2H), 7.60-7.25 (m, 2H), 6.92 (d, 1H, J=8.7 Hz), 6.47-6.39 (m, 3H), 4.54-4.52 (m, 1H), 3.76-3.58 (m, 10H), 2.27-2.05 (m, 2H). LC-MS: 247 [M/2+H]+, 493 [M+H]+, 491 [M-H]-, tR=1.22 min. HPLC: 95.20% at 214 nm, 95.06% at 254 nm, tR=5.64 min.
The synthetic route of 23814-14-4 has been constantly updated, and we look forward to future research findings.
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;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem