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 86638558 | HCID 86638558 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59175836 | HCID 59175836 | 6.5% |
Reaction Steps
(S)-1,1,1,3,3,3-Hexafluoro-2-(4-((3-methylpiperazin-1-yl)methyl)phenyl)propan-2-ol (0.854 mmol, 0.304 g), 4-(3-(cyclopropylmethyl)ureido)benzoic acid (0.854 mmol, 0.2 g) and triethylamine (2.56 mmol, 0.356 mL, 0.259 g) were combined in dichloromethane and stirred at room temperature. 1-Propanephosphonic acid cyclic anhydride (1.28 mmol, 0.762 mL, 0.815 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 (32 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08357679B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-cbd859e84b9d4cd99fe474aa5ae00bd7 |
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| Source note | uspto-grants-2013_01 |
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