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

HRID 1712682Notes

Reaction equation

HRID 1712682 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[O:7]([C:14]([NH:16][C:17]1[CH:22]=[C:21]([O:23][C:24]2[C:29]([F:30])=[CH:28][C:27]([NH:31][C:32]([C:34]3([C:37]([O:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[O:38])[CH2:36][CH2:35]3)=[O:33])=[C:26]([F:47])[CH:25]=2)[CH:20]=[CH:19][N:18]=1)=O)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>CN1CCCC1=O>[F:47][C:26]1[CH:25]=[C:24]([O:23][C:21]2[CH:20]=[CH:19][N:18]=[C:17]([NH:16][C:14]([N:4]3[CH2:5][CH2:6][C@H:2]([OH:1])[CH2:3]3)=[O:7])[CH:22]=2)[C:29]([F:30])=[CH:28][C:27]=1[NH:31][C:32]([C:34]1([C:37]([O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[O:38])[CH2:36][CH2:35]1)=[O:33]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2733874(3S)-pyrrolidin-3-olHCID 24788625Benzyl 1-({[4-([2-[(phenoxycarbonyl)amino]pyridin-4-yl}oxy)-2,5-difluorophenyl]amino}carbonyl)cyclopropanecarboxylate

Product 1

HCID 59459706Benzyl 1-[({2,5-difluoro-4-[(2-{[((S)-3-hydroxypyrrolidin-1-yl)carbonyl]amino}pyridin-4-yl)oxy]phenyl}amino)carbonyl]cyclopropanecarboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(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.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. filtrationThe precipitated solid was collected by filtration
  3. washthe solid was washed with water (20 ml, three times)
  4. customthe solid was dried by hot air (80° C.) for 1 day

Sources & evidence

ORD record
ord-b82b840b79d44db79f8233dc33a61674
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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