HCID 178465674, compound → HCID 178465673, compound

HRID 2423255Notes

Reaction equation

HRID 2423255 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:38])[C:10](=[C:26]2[NH:30][C:29]3[CH:31]=[CH:32][C:33]([N+:35]([O-])=O)=[CH:34][C:28]=3[NH:27]2)[C:11]([C:13]2[CH:14]=[C:15]([S:19]([NH:22][C:23](=[NH:25])[CH3:24])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1>[Pd].C(OCC)(=O)C>[NH2:35][C:33]1[CH:32]=[CH:31][C:29]2[NH:30][C:26](=[C:10]([C:9]([C:4]3[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=3)=[O:38])[C:11]([C:13]3[CH:14]=[C:15]([S:19]([NH:22][C:23](=[NH:25])[CH3:24])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=3)=[O:12])[NH:27][C:28]=2[CH:34]=1

Participants

4

Reactant 1

HCID 178465674HCID 178465674, compound

Product 1

HCID 178465673HCID 178465673, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Pd—C (85 mg) was added to an ethyl acetate (150 mL) suspension of N-({3-[3-(3,5-difluorophenyl)-2-(5-nitro-1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)ethanimidamide (845 mg), followed by stirring at room temperature for 22 hours under hydrogen atmosphere (1 atm). The insoluble matter was separated by filtration, washed with ethanol, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1), and recrystallized from ethyl acetate/n-hexane to obtain N-({3-[2-(5-amino-1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(3,5-difluorophenyl)-3-oxopropanoyl]phenyl}sulfonyl)ethanimidamide (667 mg).

Workup

  1. customThe insoluble matter was separated by filtration
  2. washwashed with ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)
  5. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-bf6574ab4c73448eb441b5089e70928d
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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