HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium triacetoxyborohydride → N,N-Dimethyl-4-(4-{(3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-1-yl}cyclohexyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | N,N-dimethyl-4-(4-oxocyclohexyl)benzamide | HCID 11107611 | — |
| Reactant | (R)-N-(2-oxo-2-(pyrrolidin-3-ylamino)ethyl)-3-(trifluoromethyl)benzamide | HCID 59556069 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N,N-Dimethyl-4-(4-{(3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-1-yl}cyclohexyl)benzamide | HCID 59556051 | 22% |
Reaction Steps
100 mg (0.4 mmol) of N,N-dimethyl-4-(4-oxocyclohexyl)benzamide and 126 mg (0.4 mmol) of N-{2-oxo-2-[(3R)-pyrrolidin-3-ylamino]ethyl}-3-(trifluoromethyl)benzamide were dissolved in 10 mL of methylene chloride. To the solution was added 170 mg (0.8 mmol) of sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 2 h. Direct chromatography on silica gel gave the final desired product 45 mg (top spot on TLC and first peak on HPLC), yield: 22%. MS: 545 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07985730B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-519de45e4e7f4c14bfc01e78ef12c929 |
| Source note | uspto-grants-2011_07 |