(5-Methyl-3-phenyl-4-isoxazolyl)methylamine → 2-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-thiazole-5-carboxylic acid isoprop-ylamide

HRID 1923647노트

반응식

HRID 1923647 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][NH2:14].[CH:15]([NH:18][C:19]([C:21]1[S:25][C:24](Cl)=[N:23][CH:22]=1)=[O:20])([CH3:17])[CH3:16]>CN(C=O)C>[CH:15]([NH:18][C:19]([C:21]1[S:25][C:24]([NH:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:23][CH:22]=1)=[O:20])([CH3:17])[CH3:16]

참가 물질

4

반응물 2

HCID 2776151(5-Methyl-3-phenyl-4-isoxazolyl)methylamineHCID 666437382-Chloro-thiazole-5-carboxylic acid isopropylamide

생성물 1

HCID 497809282-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-thiazole-5-carboxylic acid isoprop-ylamide수율 13.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A stirred solution of (5-methyl-3-phenyl-4-isoxazolyl)methylamine (100 mg, 0.53 mmol) and 2-chloro-thiazole-5-carboxylic acid isopropylamide (100 mg, 0.49 mmol) in DMF (5 mL) was heated at 100° C. for 7 days, then at 150° C. under microwave irradiation for 15 min. The reaction mixture was cooled and concentrated in vacuo, then diluted with water and extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated, then purified by chromatography (silica, 0 to 3% methanol in dichloromethane) to give the title compound (23 mg, 12%) as a white solid. MS: m/e=357.3 [M+H]+.

후처리

  1. customat 150° C. under microwave irradiation for 15 min
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. customThe combined organic extracts were dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by chromatography (silica, 0 to 3% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-3815fc4a75af4ff1b6aff7f46b85c884
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178522B2

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