HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → N-(4-Chloro-3-(3-(4-chloro-2-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzyl)cyclopropanecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 4-Chloro-2-fluorobenzoyl isocyanate | HCID 54541725 | — |
| Reactant | Tert-butyl 2-(2-chloro-5-(cyclopropanecarboxamidomethyl) phenyl)hydrazinecarboxylate | HCID 90019289 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(4-Chloro-3-(3-(4-chloro-2-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzyl)cyclopropanecarboxamide | HCID 136246028 | 55.9% |
Reaction Steps
The title compound was prepared by following the procedure as described for Example-83 by using tert-butyl 2-(2-chloro-5-(cyclopropanecarboxamidomethyl)phenyl)hydrazinecarboxylate (step-7 of Intermediate-48, 0.060 g, 0.17 mmol), 4-chloro-2-fluorobenzoyl isocyanate (Intermediate-58, 0.035 g, 0.71 mmol), DCM (10 mL) and TFA (3 mL) to afford 0.040 g of desired product. 1H NMR (400 MHz, DMSO d6): δ 0.67-0.69 (m, 4H), 1.59-1.60 (m, 1H), 4.31 (d, J=5.9 Hz, 2H), 7.36 (dd, J=6.24 Hz, 1H), 7.45 (dd, J=8.5 Hz, 2H), 7.59 (d, J=8.3 Hz, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.83 (t, J=8.3 Hz, 1H), 7.64 (t, J=6 Hz, 1H), 12.51 (br s, 1H); MS (m/z): 421.08 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09096545B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-a3b83311a2f54a7cb514d7c83d5c0727 |
| Source note | uspto-grants-2015_08 |