Imidazole → HCID 58654364, 화합물

HRID 1170504노트

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HRID 1170504 반응식
C(=O)([O-])[O-].[Cs+2].[CH3:6][O:7][N:8]([CH3:17])[C:9]([C:11]1[N:12]=[C:13](Br)[S:14][CH:15]=1)=[O:10].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>CN(C=O)C.CCOC(C)=O>[CH3:6][O:7][N:8]([CH3:17])[C:9]([C:11]1[N:12]=[C:13]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[S:14][CH:15]=1)=[O:10]

참가 물질

5

반응물 2

HCID 795ImidazoleHCID 866052332-bromo-N-methoxy-N-methyl-1,3-thiazole-4-carboxamide

생성물 1

HCID 58654364HCID 58654364, 화합물수율 92%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

Cesium(II)carbonate (1.36 g, 4.18 mmol) was added to a solution of 2-bromo-thiazole-4-carboxylic acid methoxy-methyl-amide (500 mg, 1.99 mmol) and imidazole (135 mg, 1.99 mmol) in DMF (5 mL) under a nitrogen atmosphere at r.t. prior to heating at 120° C. for 40 minutes in the microwave reactor. The reaction was then cooled to r.t., diluted with EtOAc (100 mL), washed with 1M NaOH (75 mL), brine (75 mL), dried over Na2SO4, filtered and concentrated to a white solid. Purification was achieved using column chromatography (CH2Cl2 to 9:1 CH2Cl2/MeOH) to afford 435 mg (92%) of 2-imidazol-1-yl-thiazole-4-carboxylic acid methoxy-methyl-amide as a white solid. [M+H]+ 239.02.

후처리

  1. temperatureThe reaction was then cooled to r.t.
  2. washwashed with 1M NaOH (75 mL), brine (75 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a white solid
  6. customPurification

출처 및 근거

ORD 기록
ord-8b2aacf67d004a399b8931c80b874527
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825256B2

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