4-(1-naphthyl)-1H-pyrrole-3-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】33674

【品名】4-(1-naphthyl)-1H-pyrrole-3-carboxylic acid

【CA登记号】

【分子式】C₁₅H₁₁NO₂

【分子量】237.25788

【元素组成】C 75.94% H 4.67% N 5.9% O 13.49%

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：(X)

Horner-Emmons condensation of 1-naphthaldehyde (VI) with triethyl phosphonoacetate (VII) using DBU as the base afforded naphthylacrylate (VIII). This was reacted with tosylmethylisocyanide and potassium tert-butoxide to produce pyrrole (IX). Hydrolysis of the ester group of (IX) with KOH gave rise to the carboxylic acid (X), which was coupled with N-methylpiperazine (XI) employing EDC and HOBt or, alternatively, by previous conversion to the corresponding acid chloride with SOCl2. The resulting amide (XII) was finally alkylated at the pyrrole N atom with chloride (V) in the presence of NaH.

参考文献中间体

合成目标

【1】 Lee, J.; Lee, H.; Shin, Y.; et al.; Synthesis and structure-activity relationships of 1-(1(3)H-imidazole-5(4)-yl)-methylpyrroles as farnesyl protein transferase inhibitors (FTPI). 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 210.
【2】 Lee, J.H.; Yoo, J.K.; Koh, J.S.; Choi, T.S.; Shin, Y.S.; Kim, K.H.; Jung, W.H.; Kim, J.H.; Lee, S.H.; Ahn, I.A.; Ro, S.G.; Lee, H.I.; Kim, H.S.; Chung, H.H.; Jeong, S.W.; Kwak, T.H. (LG Chem Ltd.); Imidazole derivs. having an inhibitory activity for farnesyl transferase and process for preparation thereof. WO 9928315 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	33672	1-(1,3-benzodioxol-5-ylmethyl)-5-(chloromethyl)-1H-imidazole		C₁₂H₁₁ClN₂O₂	详情	详情
(VI)	12314	1-Naphthaldehyde	66-77-3	C₁₁H₈O	详情	详情
(VII)	10019	Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate	867-13-0	C₈H₁₇O₅P	详情	详情
(VIII)	25405	ethyl (E)-3-(1-naphthyl)-2-propenoate		C₁₅H₁₄O₂	详情	详情
(IX)	33673	ethyl 4-(1-naphthyl)-1H-pyrrole-3-carboxylate		C₁₇H₁₅NO₂	详情	详情
(X)	33674	4-(1-naphthyl)-1H-pyrrole-3-carboxylic acid		C₁₅H₁₁NO₂	详情	详情
(XI)	10061	1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine	109-01-3	C₅H₁₂N₂	详情	详情
(XII)	33675	(4-methyl-1-piperazinyl)[4-(1-naphthyl)-1H-pyrrol-3-yl]methanone		C₂₀H₂₁N₃O	详情	详情

Extended Information