Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Propylphosphonic anhydride | HCID 111923 | — |
| Reactant | 4-(3-(Cyclopropylmethyl)ureido)benzoic acid | HCID 58055819 | — |
| Reactant | HCID 86638557 | HCID 86638557 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59175893 | HCID 59175893 | 15.5% |
Reaction Steps
(R)-1,1,1,3,3,3-Hexafluoro-2-(4-((3-methylpiperazin-1-yl)methyl)phenyl)propan-2-ol (0.427 mmol, 0.152 g), 4-(3-(cyclopropylmethyl)ureido)benzoic acid (0.427 mmol, 0.1 g) and triethylamine (1.281 mmol, 0.178 mL, 0.130 g) were combined in dichloromethane and stirred at room temperature. 1-Propanephosphonic acid cyclic anhydride (0.640 mmol, 0.381 mL, 0.407 g; 50% solution in ethyl acetate) was added and the reaction allowed to stir for 1 hour. The reaction mixture was washed with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 5% methanol/dichloromethane) to afford the title compound (38 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08357679B2 |
|---|
| Source dataset | uspto-grants-2013_01 |
|---|
| ORD ID | ord-cb05457ccab8473aa2ca7a6780d6c980 |
|---|
| Source note | uspto-grants-2013_01 |
|---|