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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1712682Generated: October 31, 2026

Sodium Bicarbonate → Benzyl 1-[({2,5-difluoro-4-[(2-{[((S)-3-hydroxypyrrolidin-1-yl)carbonyl]amino}pyridin-4-yl)oxy]phenyl}amino)carbonyl]cyclopropanecarboxylate

https://huagongshe.com/reaction/1712682

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
Reactant(3S)-pyrrolidin-3-olHCID 2733874—
ReactantBenzyl 1-({[4-([2-[(phenoxycarbonyl)amino]pyridin-4-yl}oxy)-2,5-difluorophenyl]amino}carbonyl)cyclopropanecarboxylateHCID 24788625—
SolventN-methyl-2-pyrrolidoneHCID 13387—
ProductBenzyl 1-[({2,5-difluoro-4-[(2-{[((S)-3-hydroxypyrrolidin-1-yl)carbonyl]amino}pyridin-4-yl)oxy]phenyl}amino)carbonyl]cyclopropanecarboxylateHCID 5945970681%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07790885B2
Source datasetuspto-grants-2010_09
ORD IDord-b82b840b79d44db79f8233dc33a61674
Source noteuspto-grants-2010_09