HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → Benzyl 1-[({2,5-difluoro-4-[(2-{[((S)-3-hydroxypyrrolidin-1-yl)carbonyl]amino}pyridin-4-yl)oxy]phenyl}amino)carbonyl]cyclopropanecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (3S)-pyrrolidin-3-ol | HCID 2733874 | — |
| Reactant | Benzyl 1-({[4-([2-[(phenoxycarbonyl)amino]pyridin-4-yl}oxy)-2,5-difluorophenyl]amino}carbonyl)cyclopropanecarboxylate | HCID 24788625 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | Benzyl 1-[({2,5-difluoro-4-[(2-{[((S)-3-hydroxypyrrolidin-1-yl)carbonyl]amino}pyridin-4-yl)oxy]phenyl}amino)carbonyl]cyclopropanecarboxylate | HCID 59459706 | 81% |
Reaction Steps
(S)-3-Hydroxypyrrolidine (0.0577 ml) was added to a mixture of benzyl 1-({[4-({2-[(phenoxycarbonyl)amino]pyridin-4-yl}oxy)-2,5-difluorophenyl]amino}carbonyl)cyclopropanecarboxylate (200 mg) and N-methylpyrrolidinone (4.0 ml) at room temperature under a nitrogen atmosphere, and the mixture was stirred for 2 hours. A saturated aqueous solution of sodium hydrogencarbonate (20 ml) was added to the mixture, and the mixture was stirred for 30 minutes. The precipitated solid was collected by filtration, and the solid was washed with water (20 ml, three times), and the solid was dried by hot air (80° C.) for 1 day to give the title compound (159.0 mg, 81%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07790885B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-b82b840b79d44db79f8233dc33a61674 |
| Source note | uspto-grants-2010_09 |