HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 5-(4-Chlorophenyl)-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)furan-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 5-(4-Chlorophenyl)-2-furoic acid | HCID 726693 | — |
| Reactant | 3-Amino-N-cyclopropyl-4-methylbenzamide hydrochloride | HCID 44203194 | — |
| Solvent | Water | HCID 962 | — |
| Product | 5-(4-Chlorophenyl)-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)furan-2-carboxamide | HCID 59761390 | 98.8% |
Reaction Steps
To a solution of 5-(4-chlorophenyl)furan-2-carboxylic acid (45 mg, 0.20 mmol) and 3-amino-N-cyclopropyl-4-methylbenzamide hydrochloride (prepared as described in WO 04/071440) (50 mg, 0.22 mmol) in DMF (0.5 mL) DIPEA (0.105 mL, 0.6 mmol) and the resulting mixture was stirred at rt for 1 h then at 80° C. for 1 h. The reaction was cooled to rt and water (3 mL) was added and the crude product was collected by vacuum filtration and dried under vacuum to afford 78 mg of a tan solid. The crude product was recrystallized from CH2Cl2 to afford 48 mg of a light tan solid as the title compound (Example 127). HPLC Ret. Time=3.52 min, LCMS [M+H]+ 395.23.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07935696B2 |
| Source dataset | uspto-grants-2011_05 |
| ORD ID | ord-6a29ff00ffe549b6b8db83f4aee06917 |
| Source note | uspto-grants-2011_05 |