1-(2,3,5,6-tetramethylbenzyl)-1H-indole-4-carbaldehyde -Drug Synthesis Database

【结构式】

【分子编号】62818

【品名】1-(2,3,5,6-tetramethylbenzyl)-1H-indole-4-carbaldehyde

【CA登记号】

【分子式】C₂₀H₂₁NO

【分子量】291.39288

【元素组成】C 82.44% H 7.26% N 4.81% O 5.49%

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：(III)

Alkylation of the sodium salt of indole-4-carbaldehyde (I) with 2,3,5,6-tetramethylbenzyl chloride (II) affords the N-alkylated indole aldehyde (III). Subsequent condensation of aldehyde (III) with 3-cyano-4-hydroxybenzoic acid hydrazide (IV) in DMSO in the presence of an acidic catalyst yields the target acyl hydrazone.

参考文献中间体

合成目标

【1】 Madsen, P.; Ling, A.; Plewe, M.; et al.; Optimization of alkylidene hydrazide based human glucagon receptor antagonists. Discovery of the highly potent orally available 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6-tetramethylbenzyl)-1H-indol-4-ylmethylene]hydrazide. J Med Chem 2002, 45, 26, 5755.
【2】 Lau, J.; Madsen, P.; Truesdale, L.K.; Sams, C.; Feng, J.; Kiel, D.; Ling, A.; Kukl, A.; Shi, S.; Plewe, M.B.; May, J. (Agouron Pharmaceuticals, Inc.; Novo Nordisk A/S); Glucagon antagonists/inverse agonists. JP 2002533439; WO 0039088 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	62816	1H-indole-4-carbaldehyde	C₉H₇NO	详情	详情
(II)	62817	3-(chloromethyl)-1,2,4,5-tetramethylbenzene	C₁₁H₁₅Cl	详情	详情
(III)	62818	1-(2,3,5,6-tetramethylbenzyl)-1H-indole-4-carbaldehyde	C₂₀H₂₁NO	详情	详情
(IV)	60848	3-cyano-4-hydroxybenzohydrazide	C₈H₇N₃O₂	详情	详情

Extended Information