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

HRID 1923647ノート

反応式

HRID 1923647 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-3815fc4a75af4ff1b6aff7f46b85c884
出典データセット
uspto-grants-2012_05
特許番号
US08178522B2

反応ノート

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