Trimethyl orthoacetate → Benzoic acid, 4-[2-[4-(2-methoxyethyl)-1-piperazinyl]-4-thiazolyl]-

HRID 606570ノート

反応式

HRID 606570 の反応式
[CH3:1][O:2][C:3](OC)(OC)[CH3:4].[N:9]1([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=3)[N:19]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C([BH3-])#N.[Na+]>Cl.C(#N)C.C([O-])(=O)C.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][N:12]1[CH2:13][CH2:14][N:9]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:27][CH:28]=3)[N:19]=2)[CH2:10][CH2:11]1

参加物

7

反応物 3

HCID 15050Trimethyl orthoacetateHCID 5003444Sodium cyanoborohydrideHCID 670474804-[2-(Piperazin-1-yl)-1,3-thiazol-4-yl]benzoic acid

生成物 1

HCID 11653147Benzoic acid, 4-[2-[4-(2-methoxyethyl)-1-piperazinyl]-4-thiazolyl]-収率 51.8%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 6342Acetonitrile溶媒HCID 517045Sodium Acetate溶媒

反応条件

温度
50 °C

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. temperatureto cool to RT
  2. stirringthe reaction stirred at RT for 16 h
  3. concentrationThe reaction was concentrated in vacuo
  4. customthe product purified by flash chromatography (silica gel, 10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-185e9e6e50c5478fb233f0c9c0c1b0dc
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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