Methanol → 1-Isopropylsulfonyl-2-amino-6-(2-(methyl)-5-(2,4-difluorophenyl)-imidazol-4-yl)-benzimidazole methanesulfonate

HRID 2252082Notes

Reaction equation

HRID 2252082 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([CH3:36])[N:19](CC4C=CC=CC=4)[C:20]=3[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:37])(=[O:6])=[O:5])([CH3:3])[CH3:2].[H][H].C[OH:41]>[Pd]>[CH3:1][S:4]([OH:6])(=[O:41])=[O:5].[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([CH3:36])[NH:19][C:20]=3[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:37])(=[O:6])=[O:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 179817511-Isopropylsulfonyl-2-amino-6-(1-(benzyl)-2-(methyl)-5-(2,4-difluorophenyl)-imidazol-4-yl)-benzimidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 179816391-Isopropylsulfonyl-2-amino-6-(2-(methyl)-5-(2,4-difluorophenyl)-imidazol-4-yl)-benzimidazole methanesulfonateYield 47%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 1-isopropylsulfonyl-2-amino-6-(1-(benzyl)-2-(methyl)-5-(2,4-difluorophenyl)-imidazol-4-yl)-benzimidazole (390 mg, 0.75 mmol) in 100 mL methanol add palladium black (390 mg), and hydrogen gas at 50° C. overnight at 60 psi. The solution is filtered and purified by radial chromatography eluting with 8% methanol in methylene chloride to yield 152 mg (47%) of the title compound as an off-white solid. MS(ES+): m/z=432.0 (M+H)+

Workup

  1. filtrationThe solution is filtered
  2. custompurified by radial chromatography
  3. washeluting with 8% methanol in methylene chloride

Sources & evidence

ORD record
ord-f216bc4ac7794f31877e6c9d4c998871
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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