2-[3-[1,1'-biphenyl]-4-yl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]acetyl chloride -Drug Synthesis Database

【结构式】

【分子编号】51033

【品名】2-[3-[1,1'-biphenyl]-4-yl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]acetyl chloride

【CA登记号】

【分子式】C₂₄H₁₆ClF₃N₂O

【分子量】440.8518296

【元素组成】C 65.39% H 3.66% Cl 8.04% F 12.93% N 6.35% O 3.63%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

Condensation of phenetidine (I) with 1-ethynyl-1-chlorocyclohexane (II) by means of CuCl and Et3N gave the propargyl aniline (III). This was then cyclized in the presence of copper catalyst in refluxing toluene to furnish the target dihydroquinoline.

参考文献中间体

合成目标

【1】 Dorey, G.; Lestage, P.; Casara, P.; Lockhart, B.; New quinolinic derivatives as centrally active antioxidants. Bioorg Med Chem Lett 2000, 10, 9, 935.
【2】 Lestage, P.; Dorey, G.; Casara, P.; Lockhart, B. (ADIR et Cie.); Derivs. of dihydro- and tetrahydrochinoline as a medicinal antioxidants. EP 0995743; FR 2784988; JP 2000128865 .

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)	45939	4-Aminophenetole; 1-Amino-4-ethoxybenzene; 4-Aminoethoxybenzene; 4-Ethoxyphenylamine; p-Phenetidine; 4-Ethoxyaniline	156-43-4	C₈H₁₁NO	详情	详情
(II)	51033	2-[3-[1,1'-biphenyl]-4-yl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]acetyl chloride		C₂₄H₁₆ClF₃N₂O	详情	详情
(III)	51034			C₄₈H₈₀O₄₀	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

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.

参考文献中间体

合成目标

【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

Extended Information