【结 构 式】 |
【分子编号】51028 【品名】1-[1,1'-biphenyl]-4-yl-1-ethanone N-[3-(trifluoromethyl)phenyl]hydrazone 【CA登记号】 |
【 分 子 式 】C21H17F3N2 【 分 子 量 】354.3746696 【元素组成】C 71.18% H 4.84% F 16.08% N 7.91% |
合成路线1
该中间体在本合成路线中的序号:(III)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 |