Ethanol → HCID 21905381, compound

HRID 1247421Notes

Reaction equation

HRID 1247421 reaction equation
[F:1][C:2]1[C:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[C:4]([F:15])[C:3]=1[CH:16]([O:31][CH3:32])[C:17]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[NH:30])[NH:28]O)=[CH:23][CH:22]=1)=[O:18].C([OH:35])C>C(O)(=O)C.[Ni]>[C:16]([OH:31])(=[O:35])[CH3:17].[C:27]([C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:19][C:17](=[O:18])[CH:16]([C:3]2[C:4]([F:15])=[CH:5][CH:6]=[C:7]([NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:2]=2[F:1])[O:31][CH3:32])=[CH:26][CH:25]=1)(=[NH:28])[NH2:30]

Participants

5

Reactant 2

HCID 702EthanolHCID 178496440HCID 178496440, compound

Product 1

HCID 21905381HCID 21905381, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 935NickelCatalyst

Procedure

To a stirred solution of (RS)-2-(2,6-difluoro-3-phenylamino-phenyl)-N-[4-(N-hydroxycarbamimidoyl)-benzyl]-2-methoxy-acetamide (106 mg) at rt in ethanol (5 ml) under an argon atmosphere were added 5 drops of acetic acid and and a catalytic amount of Raney-Nickel. The mixture was then stirred at rt under a hydrogen atmosphere for 23 h. The catalyst was filtered off and the filtrate was concentrated. The crude product was purified using flash chromatography (EtOAc/acetone/H2O/HOAc 6:2:1:1) to give (RS)-N-(4-carbamimidoyl-benzyl)-2-(2,6-difluoro-3-phenylamino-phenyl)-2-methoxy-acetamide acetate (92 mg) as on off-white solid. MS 425.5 ([M+H]+)

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified

Sources & evidence

ORD record
ord-9851807397d546d6b8dd7bff07a537b1
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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