Acetic Acid → 4-((4-Chlorobenzyl)oxy)-1-(1,2-dimethyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2202935Notes

Reaction equation

HRID 2202935 reaction equation
CN(C(ON1N=[N:16][C:11]2[CH:12]=C[CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NC1C=CC(N2C=C[C:35]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=3)=CC2=O)=CC=1NC.[CH:50]([N:53]([CH2:57][CH3:58])[CH:54]([CH3:56])[CH3:55])([CH3:52])C.[CH3:59][C:60](O)=O.CN(C=[O:67])C>O>[Cl:46][C:43]1[CH:42]=[CH:41][C:40]([CH2:39][O:38][C:35]2[CH:58]=[CH:57][N:53]([C:54]3[CH:55]=[CH:12][C:11]4[N:16]=[C:60]([CH3:59])[N:15]([CH3:14])[C:10]=4[CH:56]=3)[C:50](=[O:67])[CH:52]=2)=[CH:45][CH:44]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896902584-(4-Chlorobenzyloxy)-1-(4-amino-3-(methylamino)phenyl)pyridin-2(1h)-one

Product 1

HCID 896909704-((4-Chlorobenzyl)oxy)-1-(1,2-dimethyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

HATU (321 mg) was added to a solution of 1-(4-amino-3-(methylamino)phenyl)-4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (250 mg), N,N-diisopropylethylamine (0.367 ml) and AcOH (0.044 ml) in DMF (3 ml) at room temperature. The mixture was stirred at room temperature for 2 h. Water (6 ml) was added to the mixture. The precipiate was collected by filtration and dissolved to AcOH (3 ml). The mixture was stirred at 80° C. for 1 h. After evaporation of the solvent, the residue was purified by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOH to give the title compound (140 mg) as a pale pink solid.

Workup

  1. filtrationThe precipiate was collected by filtration
  2. dissolutiondissolved to AcOH (3 ml)
  3. stirringThe mixture was stirred at 80° C. for 1 h
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by NH silica gel column chromatography (hexane/EtOAc)
  6. customThe resulting solid was recrystallized from EtOH

Sources & evidence

ORD record
ord-0e8d560f7bf24ff4a4956af4f0da0788
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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