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【结 构 式】

【分子编号】51029

【品名】3-[1,1'-biphenyl]-4-yl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazole-4-carbaldehyde

【CA登记号】

【 分 子 式 】C23H15F3N2O

【 分 子 量 】392.3801896

【元素组成】C 70.4% H 3.85% F 14.53% N 7.14% O 4.08%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IV)

Condensation between 4-acetylbiphenyl (I) and 3-(trifluoromethyl)phenyl hydrazine (II) provided the corresponding hydrazone (III). Subsequent Vilsmeier-Haack reaction of (III) with POCl3 and DMF afforded the pyrazole aldehyde (IV). This was subjected to a Knoevenagel condensation with malonic acid to give the pyrazolylacrylic acid (V). Treatment of (V) with sulfur and ammonium hydroxide under Willgerodt-Kindler conditions led to the pyrazolylacetamide derivative (VI), which was further hydrolyzed to carboxylic acid (VII) using H2SO4 in aqueous HOAc. After conversion of (VII) to the corresponding acid chloride (VIII), condensation with dimethylamine in CH2Cl2 gave the title amide.

1 Bebernitz, G.R.; et al.; The effect of 1,3-diaryl-[1H]-pyrazole-4-acetamides on glucose utilization in ob/ob mice. J Med Chem 2001, 44, 16, 2601.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 36916 1-[1,1'-biphenyl]-4-yl-1-ethanone 92-91-1 C14H12O 详情 详情
(II) 44088 1-[3-(trifluoromethyl)phenyl]hydrazine 368-78-5 C7H7F3N2 详情 详情
(III) 51028 1-[1,1'-biphenyl]-4-yl-1-ethanone N-[3-(trifluoromethyl)phenyl]hydrazone C21H17F3N2 详情 详情
(IV) 51029 3-[1,1'-biphenyl]-4-yl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazole-4-carbaldehyde C23H15F3N2O 详情 详情
(V) 51030 (E)-3-[3-[1,1'-biphenyl]-4-yl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]-2-propenoic acid C25H17F3N2O2 详情 详情
(VI) 51031 2-[3-[1,1'-biphenyl]-4-yl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]acetamide C24H18F3N3O 详情 详情
(VII) 51032 2-[3-[1,1'-biphenyl]-4-yl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]acetic acid C24H17F3N2O2 详情 详情
(VIII) 51033 2-[3-[1,1'-biphenyl]-4-yl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]acetyl chloride C24H16ClF3N2O 详情 详情
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