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

HRID 1923647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1923647
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 497809282-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-thiazole-5-carboxylic acid isoprop-ylamideAusbeute 13,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3815fc4a75af4ff1b6aff7f46b85c884
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178522B2

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