Diisopropylethylamine → 4-(4-Fluorobenzyloxy)-1-(2-(4-ethyloxazol-5-yl)-1-methyl-1h-benzo[d]imidazol-6-yl)pyridin-2(1h)-one

HRID 2203028Notes

Reaction equation

HRID 2203028 reaction equation
[NH2:1][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].[CH2:26]([C:28]1[N:29]=[CH:30][O:31][C:32]=1[C:33](O)=O)[CH3:27].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:26]([C:28]1[N:29]=[CH:30][O:31][C:32]=1[C:33]1[N:24]([CH3:25])[C:3]2[CH:4]=[C:5]([N:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]4[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=4)=[CH:10][C:9]3=[O:23])[CH:6]=[CH:7][C:2]=2[N:1]=1)[CH3:27]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534346434-Ethyl-1,3-oxazole-5-carboxylic acidHCID 896902791-(4-Amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one

Product 1

HCID 897025794-(4-Fluorobenzyloxy)-1-(2-(4-ethyloxazol-5-yl)-1-methyl-1h-benzo[d]imidazol-6-yl)pyridin-2(1h)-oneYield 17.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (67.9 mg), 4-ethyl-1,3-oxazole-5-carboxylic acid (28.2 mg), HATU (80.0 mg), N,N-diisopropylethylamine (0.105 ml) and DMF (2.0 ml) was stirred at room temperature for 2 h. The mixture was poured into saturated NaHCO3 solution and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated in vacuo. The residue was dissolved in AcOH (1.5 ml), and the mixture was stirred at 80° C. for 1 h. The mixture was concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH). The resulting solid was recrystallized from EtOAc-hexane to give the title compound (15.7 mg) as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in AcOH (1.5 ml)
  6. stirringthe mixture was stirred at 80° C. for 1 h
  7. concentrationThe mixture was concentrated in vacuo
  8. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc
  9. customThe resulting solid was recrystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-27518b4adc924c468e89ccb7913ade3f
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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