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【结 构 式】

【分子编号】50275

【品名】 

【CA登记号】

【 分 子 式 】C19H19N3O4

【 分 子 量 】353.37768

【元素组成】C 64.58% H 5.42% N 11.89% O 18.11%

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:(VI)

Indolinone intermediate (VII): 1. The reductoalkylation of 4-ethoxyaniline (I) with benzaldehyde and NaBH4 in methanol gives the protected aniline (II), which is condensed with methoxymalonyl chloride (III) by means of TEA in dichloromethane to yield the malonamic derivative (IV). The reaction of (IV) with methanesulfonyl azide (V) and TEA affords the diazo compound (VI), which is finally submitted to a decarboxylative cyclization by means of Nafion H (a perfluorinated ion exchange resin) to provide the target indolinone intermediate (VII). 2. The condensation of the protected aniline (II) with diketene (VIII) by means of TEA in THF gives the 3-oxobutyramide (IX), which is treated with methanesulfonyl azide (V) and TEA to yield the diazo compound (X). The deacylation of (X) with KOH in acetonitrile affords the diazoacetamide (XI), which is finally cyclized to the target indolinone intermediate (VII) by means of Rh(OAc)2 in dichloromethane.

1 Venkatesan, H.; et al.; Total synthesis of SR 121463 A, a highly potent and selective vasopressin V2 receptor antagonist. J Org Chem 2001, 66, 11, 3653.
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) 50271 N-benzyl-4-ethoxyaniline; N-benzyl-N-(4-ethoxyphenyl)amine C15H17NO 详情 详情
(III) 50272 Malonic acid monomethyl ester chloride; Methyl (chloroformyl)acetate; Methyl malonyl chloride ;Methyl 3-chloro-3-oxopropionate 37517-81-0 C4H5ClO3 详情 详情
(IV) 50273 methyl 3-(benzyl-4-ethoxyanilino)-3-oxopropanoate C19H21NO4 详情 详情
(V) 50274 methanesulfonyl azide CH3N3O2S 详情 详情
(VI) 50275   C19H19N3O4 详情 详情
(VII) 50276 1-benzyl-5-ethoxy-1,3-dihydro-2H-indol-2-one C17H17NO2 详情 详情
(VIII) 11367 4-Methylene-2-oxetanone; Acetyl ketene 674-82-8 C4H4O2 详情 详情
(IX) 50277 N-benzyl-N-(4-ethoxyphenyl)-3-oxobutanamide C19H21NO3 详情 详情
(X) 50278   C19H19N3O3 详情 详情
(XI) 50279   C17H17N3O2 详情 详情
Extended Information