Water → 4-((4-Fluorobenzyl)oxy)-1-(1-methyl-2-(trichloromethyl)-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2202884Notes

Reaction equation

HRID 2202884 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[CH:10][C:9]2=[O:23])=[CH:4][C:3]=1[NH:24][CH3:25].[Cl:26][C:27]([Cl:33])([Cl:32])[C:28](=[NH:31])OC.O>CC(O)=O>[F:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][C:11]2[CH:12]=[CH:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]4[N:31]=[C:28]([C:27]([Cl:26])([Cl:32])[Cl:33])[N:24]([CH3:25])[C:3]=4[CH:4]=3)[C:9](=[O:23])[CH:10]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 100479Methyl 2,2,2-trichloroacetimidateHCID 896902791-(4-Amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one

Product 1

HCID 896900684-((4-Fluorobenzyl)oxy)-1-(1-methyl-2-(trichloromethyl)-1H-benzimidazol-6-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (270 mg) in AcOH (3 ml) was added methyl 2,2,2-trichloroacetimidate (0.196 ml) dropwise at 0° C. The mixture was stirred at room temperature for 2 h. Water was added to the mixture. The resulting precipitate was collected by filtration and dried to give the title compound (220 mg) as an ivory solid.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-bc1649a6ebd542a4afd4136a31abd025
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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