HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → tert-Butyl [1-({3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}carbonyl)cyclopropyl]carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid | HCID 688396 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | N-{5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide | HCID 66701397 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-Butyl [1-({3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}carbonyl)cyclopropyl]carbamate | HCID 68075150 | — |
Reaction Steps
125 mg (0.62 mmol) of 1-[(tert-butoxycarbonyl)amino]cyclopropanecarboxylic acid together with 295 mg (0.78 mmol) of HATU and 127 mg (1.03 mmol) of 4-dimethylaminopyridine were initially charged in 8 ml of DMF, and 180 mg (0.52 mmol) of N-{5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide were added. The reaction mixture was stirred overnight at RT and then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 179 mg (65% of theory)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987248B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-8ea063b93a354571a54fa3ca7b829174 |
| Source note | uspto-grants-2015_03 |