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

HRID 606570노트

반응식

HRID 606570 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6342Acetonitrile용매HCID 517045Sodium Acetate용매

반응 조건

온도
50 °C

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. 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)

출처 및 근거

ORD 기록
ord-185e9e6e50c5478fb233f0c9c0c1b0dc
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915300B2

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