HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → N-(4-chloro-3-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzyl)-2,2,2-trifluoroacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 2-Chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate | HCID 90019286 | — |
| Reactant | tert-Butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate | HCID 90019516 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(4-chloro-3-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzyl)-2,2,2-trifluoroacetamide | HCID 136246025 | 41.5% |
Reaction Steps
The title compound was prepared according to the procedure described for Example-83 by using tert-butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate (Intermediate-53, 1.00 g, 3.63 mmol), 2-chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate (step-3 of Intermediate-26, 1.30 g, 4.03 mmol), DCM (20 mL) and TFA (5.0 mL) to afford 0.700 g of the desired product. 1H NMR (400 MHz, DMSO d6): δ 4.44-4.46 (d, J=6 Hz, 2H), 7.48-7.50 (d, J=8.4 Hz, 1H), 7.65-7.68 (m, 2H), 7.84-7.86 (d, J=8.8 Hz, 2H), 8.17-8.19 (d, J=8.4 Hz, 2H), 10.05 (br s, 1H), 12.69 (br s, 1H); MS (m/z): 463.17 (M−H−).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09096545B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-9ba8925edc014ee782fb2516b8e8547b |
| Source note | uspto-grants-2015_08 |