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

HRID 1923647Notes

Reaction equation

HRID 1923647 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-3815fc4a75af4ff1b6aff7f46b85c884
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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