4-[4-(4-Fluorophenylaminocarbonyl)piperazin-1-yl]-7-nitroquinolin trifluoroacetate → 7-Amino-4-[4-(4-fluorophenylaminocarbonyl)piperazin-1-yl]quinoline

HRID 1353324Notes

Reaction equation

HRID 1353324 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[C:33]4[C:28](=[CH:29][C:30]([N+:34]([O-])=O)=[CH:31][CH:32]=4)[N:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[O:17])=[CH:11][CH:10]=1.[H][H]>CO.[Pd]>[NH2:34][C:30]1[CH:29]=[C:28]2[C:33]([C:24]([N:21]3[CH2:20][CH2:19][N:18]([C:16]([NH:15][C:12]4[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=4)=[O:17])[CH2:23][CH2:22]3)=[CH:25][CH:26]=[N:27]2)=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 211016944-[4-(4-Fluorophenylaminocarbonyl)piperazin-1-yl]-7-nitroquinolin trifluoroacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 211017417-Amino-4-[4-(4-fluorophenylaminocarbonyl)piperazin-1-yl]quinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-[4-(4-fluorophenylaminocarbonyl)piperazin-1-yl]-7-nitroquinoline trifluoroacetate (130 mg) and 10% Pd/C (20 mg) in MeOH is stirred in a hydrogen atmosphere for 30 min. The reaction mixture is filtered and concentrated giving the title product.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-551c8c35c7ba464fa68793cde9b2539c
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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