Sodium Hydroxide → HCID 178474191, compound

HRID 2099857Notes

Reaction equation

HRID 2099857 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[O:44])[C:12](=[C:23]2[NH:27][C:26]3[CH:28]=[CH:29][C:30]([NH:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([NH:40][C:41](=[O:43])[CH3:42])=[CH:36][CH:35]=4)=[CH:31][C:25]=3[NH:24]2)[C:13]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)=[O:14])[CH:6]=1)(=O)C.[OH-].[Na+].[Cl-].[NH4+]>C1COCC1>[F:22][C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([F:21])[CH:18]=1)[C:13]([C:12](=[C:23]1[NH:27][C:26]2[CH:28]=[CH:29][C:30]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([NH:40][C:41](=[O:43])[CH3:42])=[CH:36][CH:35]=3)=[CH:31][C:25]=2[NH:24]1)[C:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([OH:4])[CH:6]=1)=[O:44])=[O:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 178474192HCID 178474192, compound

Product 1

HCID 178474191HCID 178474191, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution (5 ml) of 3-{2-[5-(4-acetylaminobenzylamino)-1,3-dihydro-2H-benzimidazol-2-ylidene]-3-(3,5-difluorophenyl)-3-oxopropionyl}phenyl acetate (123 mg) was added 1M sodium hydroxide aqueous solution (0.5 ml), followed by 24 hours of stirring. A saturated ammonium chloride aqueous solution was added thereto, followed by extraction with ethyl acetate and drying over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: chloroform:methanol=20:1 (v/v)) to obtain N-[4-({2-[1-(3,5-difluorobenzoyl)-2-(3-hydroxyphenyl)-2-oxoethylidene]-2,3-dihydro-1H-benzimidazol-5-ylamino}methyl)phenyl]acetamide (98 mg, 86%). Hereinafter, the compound of Example 438 was obtained similarly.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (eluent: chloroform:methanol=20:1 (v/v))

Sources & evidence

ORD record
ord-4d74618ea318458eaa5aa7a1e328a366
Source dataset
uspto-grants-2009_08
Patent number
US07569688B2

Reaction notes

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