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【结 构 式】

【分子编号】60051

【品名】5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid

【CA登记号】

【 分 子 式 】C7H7NO3

【 分 子 量 】153.13752

【元素组成】C 54.9% H 4.61% N 9.15% O 31.34%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XI)

Vilsmeier-Haack formylation of ethyl 4-methylpyrrole-2-carboxylate (IX) using POCl3 in DMF furnished the pyrrole aldehyde (X). Subsequent basic hydrolysis of the ethyl ester group of (X) gave 5-formyl-4-methylpyrrole-2-carboxylic acid (XI), which was further coupled to cis-2,6-dimethylpiperazine (XII) producing amide (XIII). The title compound was finally prepared by aldol condensation between the pyrrole aldehyde (XIII) and lactam (VIII) in the presence of piperidine.

1 Wei, C.C.; Tang, P.C.; McMahon, G.; Sun, L.; Hirth, K.P.; Liang, C.; Cui, J. (Sugen, Inc.); 4-Substd. 7-aza-indolin-2-ones and their use as protein kinase inhibitors. EP 1244672; WO 0146196 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 60852 4-(3-chloro-4-fluoroanilino)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one C12H8ClFN4O 详情 详情
(IX) 60049 ethyl 4-methyl-1H-pyrrole-2-carboxylate C8H11NO2 详情 详情
(X) 60050 ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylate C9H11NO3 详情 详情
(XI) 60051 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid C7H7NO3 详情 详情
(XII) 20848 (2R,6S)-2,6-dimethylpiperazine C6H14N2 详情 详情
(XIII) 60853 5-{[(3R,5S)-3,5-dimethylpiperazinyl]carbonyl}-3-methyl-1H-pyrrole-2-carbaldehyde C13H19N3O2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(X)

Vilsmeier formylation of ethyl 4-methylpyrrole-2-carboxylate (VIII) affords aldehyde (IX). The ethyl ester group of (IX) is subsequently hydrolyzed under alkaline conditions to provide acid (X). Coupling of (X) with 4-(2-aminoethyl)morpholine (XI) gives amide (XII). Then, condensation between aldehyde (XII) and lactam (VII) in the presence of piperidine leads to adduct (XIII). The 4-chloro group of (XIII) is finally displaced with 3-chloro-4-fluoroaniline (XIV) in hot NMP to provide the title compound

1 Wei, C.C.; Tang, P.C.; McMahon, G.; Sun, L.; Hirth, K.P.; Liang, C.; Cui, J. (Sugen, Inc.); 4-Substd. 7-aza-indolin-2-ones and their use as protein kinase inhibitors. EP 1244672; WO 0146196 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 60048 4-chloro-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one C6H4ClN3O 详情 详情
(VIII) 60049 ethyl 4-methyl-1H-pyrrole-2-carboxylate C8H11NO2 详情 详情
(IX) 60050 ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylate C9H11NO3 详情 详情
(X) 60051 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid C7H7NO3 详情 详情
(XI) 12880 4-(2-Aminoethyl)morpholine; 2-(4-Morpholinyl)ethylamine; 2-(4-Morpholinyl)-1-ethanamine; N-(2-Aminoethyl)morpholine; N-Morpholine ethanamide 2038-03-1 C6H14N2O 详情 详情
(XII) 59999 5-formyl-4-methyl-N-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-carboxamide C13H19N3O3 详情 详情
(XIII) 59998 5-[(4-chloro-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-ylidene)methyl]-4-methyl-N-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-carboxamide C19H21ClN6O3 详情 详情
(XIV) 18688 3-Chloro-4-fluorophenylamine; 3-Chloro-4-fluoroaniline 367-21-5 C6H5ClFN 详情 详情
Extended Information