HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → N-(3,4,5-Trimethoxyphenyl)-3-(5-methyl-3-(2-fluoro-4-bromo-phenyl)isoxazol-4-oyl)aminophenyl Acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 2-(3-aminophenyl)-N-(3,4,5-trimethoxyphenyl)acetamide | HCID 18756260 | — |
| Reactant | 4-Carboxy-5-methyl-3-(2-fluoro-4-bromophenyl)isoxazole | HCID 18756285 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(3,4,5-Trimethoxyphenyl)-3-(5-methyl-3-(2-fluoro-4-bromo-phenyl)isoxazol-4-oyl)aminophenyl Acetamide | HCID 60083763 | 66% |
Reaction Steps
In a fashion similar to that described for preparation 35, 4-carboxy-5-methyl-3-(2-fluoro-4-bromophenyl)isoxazole (119 mg, 0.40 mmol), oxalyl chloride (0.070 ml, 0.80 mmol), dimethylformamide (0.010 ml), dichloromethane (5 ml), 2-(3-aminophenyl)-N-(3,4,5-trimethoxyphenyl)acetamide (110 mg, 0.35 mmol), triethylamine (0.111 ml, 0.80 mmol), DMAP (5 mg), dimethylformamide (1 ml), dichloromethane (5 ml) gave the title compound (138 mg, 66%) after column chromatography (silica gel, hexanes/ethyl acetate gradient).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06670373B1 |
| Source dataset | uspto-grants-2003_12 |
| ORD ID | ord-a989a6e051da4432a223da94deb17734 |
| Source note | uspto-grants-2003_12 |