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 86638571 | HCID 86638571 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59175839 | HCID 59175839 | 22.4% |
Reaction Steps
To a stirring solution of 4-(3-(cyclopropylmethyl)ureido)benzoic acid (0.337 mmol, 79 mg), 1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-2-one (0.281 mmol, 100 mg) and triethylamine (0.842 mmol, 85 mg) in dichloromethane (10 ml) was added 1-propanephosphonic acid cyclic anhydride (0.421 mmol, 268 mg; 50% solution in ethyl acetate). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane (20 mL) and washed with saturated aqueous sodium hydrogen carbonate solution (30 mL). The organic phase was concentrated and the resulting residue was purified by column chromatography on silica gel (eluting with 5% methanol/95% dichloromethane) to afford the title compound (36 mg). MS (ESI) m/z 573.0 [M+H]+
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-17937476791e4218aeb927f1ad51d801 |
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| Source note | uspto-grants-2013_01 |
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