반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]([C:11](=O)[CH2:12][O:13][CH3:14])=[C:5](OC)[CH2:6][O:7][CH3:8].[Br:17][C:18]1[CH:19]=[C:20]([NH:24][NH2:25])[CH:21]=[CH:22][CH:23]=1>>[CH3:1][O:2][C:3]([C:4]1[C:5]([CH2:6][O:7][CH3:8])=[N:25][N:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([Br:17])[CH:19]=2)[C:11]=1[CH2:12][O:13][CH3:14])=[O:16]참가 물질
실험 절차
In analogy to the procedures described for intermediates 1A-E, the title compound has been obtained by i) condensation of methyl 4-methoxyacetoacetate with methoxyacetyl chloride to give 4-methoxy-2-(2-methoxy-acetyl)-3-oxo-butyric acid methyl ester; ii) methylation of 4-methoxy-2-(2-methoxy-acetyl)-3-oxo-butyric acid methyl ester with methyl trifluoromethanesulfonate to give (E and/or Z)-3,4-dimethoxy-2-(2-methoxy-acetyl)-but-2-enoic acid methyl ester; iii) condensation of (E and/or Z)-3,4-dimethoxy-2-(2-methoxy-acetyl)-but-2-enoic acid methyl ester with (3-bromo-phenyl)-hydrazine to give 1-(3-bromo-phenyl)-3,5-bis-methoxymethyl-1H-pyrazole-4-carboxylic acid methyl ester; iv) reaction of 1-(3-bromo-phenyl)-3,5-bis-methoxymethyl-1H-pyrazole-4-carboxylic acid methyl ester with (E)-2-(4-chlorophenyl)vinyl boronic acid to give 1-{3-[(E)-2-(4-chloro-phenyl)-vinyl]-phenyl}-3,5-bis-methoxymethyl-1H-pyrazole-4-carboxylic acid methyl ester; v) saponification of 1-{3-[(E)-2-(4-chloro-phenyl)-vinyl]-phenyl}-3,5-bis-methoxymethyl-1H-pyrazole-4-carboxylic acid methyl ester to give the title compound as light brown solid. MS: 411.2 ([M−H]−, 1 Cl).
출처 및 근거
- ORD 기록
- ord-8f8a1805ecc44d89b4488c580aeac726
- 출처 데이터셋
- uspto-grants-2011_07
- 특허 번호
- US07977358B2
연결된 노트
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