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1-(2-Hydroxyethyl)piperazine → 2-[4-(2-Hydroxyethyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl ester

HRID 1392958
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HRID 1392958 반응식
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.[OH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][O:9][C:7]([C:4]1[S:3][C:2]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][OH:11])[CH2:15][CH2:16]2)=[N:6][CH:5]=1)=[O:8]
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참가 물질

5

반응물 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 2773502Methyl 2-bromothiazole-5-carboxylate

생성물 1

HCID 692031852-[4-(2-Hydroxyethyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl ester수율 68.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

To a solution of methyl 2-bromothiazole-5-carboxylate 1 (222 mg, 1.00 mmol) in acetonitrile (20 mL) were added N-(2-hydroxyethyl)piperazine 14c (156 mg, 1.20 mmol) and potassium carbonate (152 mg, 1.10 mmol) under a N2 atmosphere. The reaction mixture was heated to reflux at 80° C. for 10 h. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography using silica gel to give the compound 15c (185 mg, 68.2%).

후처리

  1. temperatureThe reaction mixture was heated
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-dcd0bd5e93104dd9bf548dcb30c964eb
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07345043B2

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