HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-[3-(2-Chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-[4-(trifluoromethyl)phenyl]cyclopropyl}benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 1-(4-(Trifluoromethyl)phenyl)cyclopropanamine | HCID 53420453 | — |
| Reactant | 4-[3-(2-chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]benzoic acid | HCID 136492434 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-[3-(2-Chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-[4-(trifluoromethyl)phenyl]cyclopropyl}benzamide | HCID 136492491 | 20% |
Reaction Steps
The title compound was prepared according to the procedure described in Example-17 by using 4-[3-(2-chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]benzoic acid (Intermediate-9, 0.100 g, 0.290 mmol), THF (5 mL), di-isopropyl ethyl amine (2.0 mL), TBTU (0.193 g, 0.590 mmol) and 1-[4-(trifluoromethyl)phenyl]cyclopropanamine (Intermediate-13, 0.073 g, 0.350 mmol) to afford 0.030 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 1.35 (s, 4H), 7.36 (d, J=7.8 Hz, 2H), 7.46-7.70 (m, 5H), 8.01 (s, 4H), 9.30 (s, 1H), 12-13 (br s, 1H); MS (m/z): 515.23 (M−H)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09439890B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-960a3094353241f98cd2da58c79a5def |
| Source note | uspto-grants-2016_09 |