4-[2-(4-tert-Butoxycarbonylpiperazin-1-yl)thiazol-4-yl]benzoic acid → 4-[2-(Piperazin-1-yl)-1,3-thiazol-4-yl]benzoic acid

HRID 606569노트

반응식

HRID 606569 반응식
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[N:11]1([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][CH:24]=3)[N:18]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

참가 물질

4

반응물 1

HCID 181867194-[2-(4-tert-Butoxycarbonylpiperazin-1-yl)thiazol-4-yl]benzoic acid

생성물 1

HCID 670474804-[2-(Piperazin-1-yl)-1,3-thiazol-4-yl]benzoic acid

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

4-[4-(4-Carboxy-phenyl)-thiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (5.0 mmol) was dissolved in hydrochloric acid in dioxane (4N, 25 ml) and the reaction stirred at RT for 2 h. The reaction was concentrated in vacuo to yield 4-(2-piperazin-1-yl-thiazol-4-yl)-benzoic acid. Trimethoxyethane (6.5 mmol) was dissolved in aqueous hydrochloric acid (1N, 10 ml) and the reaction heated at 50° C. for 1.5 h. The reaction was allowed to cool to RT and was then added to a suspension of 4-(2-piperazin-1-yl-thiazol-4-yl)-benzoic acid (5.0 mmol) in acetonitrile (25 ml) and sodium acetate buffer (1N, pH 5.5, 10 ml). The reaction was stirred at RT for 1.5 h. Sodium cyanoborohydride (6.5 mol) was added and the reaction stirred at RT for 16 h. The reaction was concentrated in vacuo and the product purified by flash chromatography (silica gel, 10% methanol in dichloromethane) to give the title product as a colourless oil (0.9 g). m/z=348 (100% M+H) in MS ES+.

후처리

  1. concentrationThe reaction was concentrated in vacuo

출처 및 근거

ORD 기록
ord-810f83bfaf794e67b4c64a5e64c6e029
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915300B2

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