HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Methyl 5-isopropyl-2-{[2-fluoro-5-(trifluoromethyl)benzoyl]amino}-1,3-thiazole-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl 2-amino-5-(propan-2-yl)-1,3-thiazole-4-carboxylate | HCID 737584 | — |
| Reactant | 2-Fluoro-5-(trifluoromethyl)benzoyl Chloride | HCID 2734880 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 5-isopropyl-2-{[2-fluoro-5-(trifluoromethyl)benzoyl]amino}-1,3-thiazole-4-carboxylate | HCID 86644543 | 92.4% |
Reaction Steps
A mixture of commercially available methyl 2-amino-5-isopropylthiazole-4-carboxylate (1 g, 4.99 mmol) and 2-fluoro-5-(trifluoromethyl)benzoyl chloride (1.31 g, 5 mmol) in anhydrous CH2Cl2 (25 mL) was treated dropwise at 0° C. with triethylamine (0.84 mL, 6 mmol). The mixture was allowed to warm to room temperature and stirred for 14 hours. The mixture was then washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography and eluted with hexanes-EtOAc (1:1) to afford 1.8 g of the title compound. MS (DCI/NH3) m/z 391 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08895592B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-90faabccc9a84e2ebb5d1565039fcaf5 |
| Source note | uspto-grants-2014_11 |