HuagongsheHuagongshe Chemistry Print Report · For research reference only
(5-Methyl-3-phenyl-4-isoxazolyl)methylamine → 2-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-thiazole-5-carboxylic acid isoprop-ylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (5-Methyl-3-phenyl-4-isoxazolyl)methylamine | HCID 2776151 | — |
| Reactant | 2-Chloro-thiazole-5-carboxylic acid isopropylamide | HCID 66643738 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-thiazole-5-carboxylic acid isoprop-ylamide | HCID 49780928 | 13.2% |
Reaction Steps
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]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178522B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-3815fc4a75af4ff1b6aff7f46b85c884 |
| Source note | uspto-grants-2012_05 |