Sodium hydride → 1-methyl-6-{4-[2-(2-oxooxazolidin-3-yl)-ethoxy]-3-(trifluoromethyl)-phenyl}-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2079551Notes

Reaction equation

HRID 2079551 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[H-].[Na+].CS(O[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:28]=[C:27]([C:29]#[N:30])[C:26]3[N:31]=[CH:32][N:33]([CH3:34])[C:25]=3[CH:24]=2)=[CH:19][C:18]=1[C:35]([F:38])([F:37])[F:36])(=O)=O>CN1C(=O)CCC1>[CH3:34][N:33]1[C:25]2[CH:24]=[C:23]([C:20]3[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][N:3]4[CH2:4][CH2:5][O:1][C:2]4=[O:6])=[C:18]([C:35]([F:37])([F:38])[F:36])[CH:19]=3)[N:28]=[C:27]([C:29]#[N:30])[C:26]=2[N:31]=[CH:32]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 739492-OxazolidinoneHCID 576575602-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl methanesulfonate

Product 1

HCID 576575391-methyl-6-{4-[2-(2-oxooxazolidin-3-yl)-ethoxy]-3-(trifluoromethyl)-phenyl}-1H-imidazo[4,5-c]pyridine-4-carbonitrileYield 10.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To oxazolidin-2-one (29.7 mg) in NMP (1 ml) was added sodium hydride is (60% in parafin oil, 13.6 mg). After stirring at room temperature for 10 minutes, 2-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl methanesulfonate (100 mg) was then added and the mixture was stirred at room temperature for 14 hours. The mixture was purified directly using HPLC to give 1-methyl-6-{4-[2-(2-oxooxazolidin-3-yl)-ethoxy]-3-(trifluoromethyl)-phenyl}-1H-imidazo[4,5-c]pyridine-4-carbonitrile (10 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hours
  2. customThe mixture was purified directly using HPLC

Sources & evidence

ORD record
ord-3f8f96509335490687cd34a953425a39
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

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