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 606569ノート

反応式

HRID 606569 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

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+.

後処理

  1. concentrationThe reaction was concentrated in vacuo

出典と根拠

ORDレコード
ord-810f83bfaf794e67b4c64a5e64c6e029
出典データセット
uspto-grants-2011_03
特許番号
US07915300B2

反応ノート

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