Acetonitrile → HCID 178508159, compound

HRID 2252072Notes

Reaction equation

HRID 2252072 reaction equation
C(S([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([C:27]4[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=4[F:34])[NH:19][C:20]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:35])(=O)=O)(C)C.[OH-].[Na+].C(#N)C>O.C(OCC)(=O)C>[NH2:35][C:8]1[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]=[C:18]([C:27]4[C:28]([F:34])=[CH:29][CH:30]=[CH:31][C:32]=4[F:33])[NH:19][C:20]=3[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:12][C:11]=2[N:7]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 98270206-[2-(2,6-difluorophenyl)-5-phenyl-1H-imidazol-4-yl]-1-propan-2-ylsulfonylbenzimidazol-2-amine

Product 1

HCID 178508159HCID 178508159, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Stir a mixture of 1-isopropylsulfonyl-2-amino-6-(2-(2,6-difluorophenyl)-5-(phenyl)-imidazol-4-yl)-benzimidazole (0.07 g, 0.142 mmol) and 1.42 mL 1 N sodium hydroxide in 1:1 water:acetonitrile at 60° C. for 1 hour. Cool the mixture to room temperature and dilute with water and ethyl acetate. Extract the aqueous phase with ethyl acetate (3 times). Wash the combined organic phases sequentially with water and saturated aqueous sodium chloride, dry over sodium sulfate, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 2:1 dichloromethane:methanol to provide the title compound in 93% yield. MS(ES+): m/z=388.0 (M+H)+

Workup

  1. extractionExtract the aqueous phase with ethyl acetate (3 times)
  2. washWash the combined organic phases sequentially with water and saturated aqueous sodium chloride
  3. dry with materialdry over sodium sulfate
  4. concentrationconcentrate under reduced pressure
  5. washeluting with 2:1 dichloromethane

Sources & evidence

ORD record
ord-7e0497ec073a4318a8fb5de0968fc3f9
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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