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【结 构 式】

【分子编号】43067

【品名】N-(2-aminoethyl)-5-(3-cyanophenyl)-2-thiophenesulfonamide

【CA登记号】

【 分 子 式 】C13H13N3O2S2

【 分 子 量 】307.39724

【元素组成】C 50.8% H 4.26% N 13.67% O 10.41% S 20.86%

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:(V)

Ethylenediamine (I) was selectively monoprotected as the N-Boc derivative (II) and then coupled with sulfonyl chloride (III), yielding sulfonamide (IV). After deprotection of the Boc group of (IV) with HCl in dioxan, the resulting amine (V) was condensed with hydroxyacid (VI) by means of BOP reagent to give amide (VII). Acid deprotection of the Boc group of (VII), followed by condensation with 2,6-dichlorobenzoyl chloride (IX), provided (X). Finally, the hydroxyl group of (X) was oxidized to the title ketone employing the Dess-Martin periodinane reagent in CH2Cl2.

1 Ator, M.A.; Mallamo, J.P.; Chatterjee, S.; Tao, M.; Wells, G.; Dunn, D.; Bihovsky, R.; Siman, R.; Gu, Z.-Q; P2-Achiral, P'-extended alpha-ketoamide inhibitors of calpain I. Bioorg Med Chem Lett 1999, 9, 16, 2371.
2 Wells, G.J.; Mallamo, J.P.; Chatterjee, S.; Bihovsky, R. (Cephalon, Inc.); Peptidyl-containing alpha-ketoamide cysteine and serine protease inhibitors. US 6150378 .
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) 14574 3-methoxy-3-oxo-2-(2-thienylmethyl)propionic acid C9H10O4S 详情 详情
(II) 13241 N-Boc-ethylenediamine;tert-butyl (2-aminoethyl)carbamate;tert-butyl 2-aminoethylcarbamate; tert-Butyl n-(2-aminoethyl)carbamate 57260-73-8 C7H16N2O2 详情 详情
(III) 43065 5-(3-cyanophenyl)-2-thiophenesulfonyl chloride C11H6ClNO2S2 详情 详情
(IV) 43066 tert-butyl 2-([[5-(3-cyanophenyl)-2-thienyl]sulfonyl]amino)ethylcarbamate C18H21N3O4S2 详情 详情
(V) 43067 N-(2-aminoethyl)-5-(3-cyanophenyl)-2-thiophenesulfonamide C13H13N3O2S2 详情 详情
(VI) 43071 (3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyric acid C15H21NO5 详情 详情
(VII) 43068 tert-butyl (1S)-1-benzyl-3-[[2-([[5-(3-cyanophenyl)-2-thienyl]sulfonyl]amino)ethyl]amino]-2-hydroxy-3-oxopropylcarbamate C28H32N4O6S2 详情 详情
(VIII) 43069 (3S)-3-amino-N-[2-([[5-(3-cyanophenyl)-2-thienyl]sulfonyl]amino)ethyl]-2-hydroxy-4-phenylbutanamide C23H24N4O4S2 详情 详情
(IX) 25087 2,6-dichlorobenzoyl chloride 4659-45-4 C7H3Cl3O 详情 详情
(X) 43070 N-((1S)-1-benzyl-3-[[2-([[5-(3-cyanophenyl)-2-thienyl]sulfonyl]amino)ethyl]amino]-2-hydroxy-3-oxopropyl)-2,6-dichlorobenzamide C30H26Cl2N4O5S2 详情 详情
Extended Information