1-Methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-N-[3-(dimethylamino)propyl]-1H-pyrrole-2-carboxamide → 1-Methyl-4-{[(1-methyl-4-amino-1H-pyrrol-2-yl)carbonyl]amino}-N-[3-(dimethylamino)propyl]-1H-pyrrole-2-carboxamide

HRID 907393Notes

Reaction equation

HRID 907393 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]([CH3:18])[CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=2)=[O:9])[CH:4]=[C:3]1[C:19]([NH:21][CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[O:20]>CO.[Pd]>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]([CH3:18])[CH:12]=[C:13]([NH2:15])[CH:14]=2)=[O:9])[CH:4]=[C:3]1[C:19]([NH:21][CH2:22][CH2:23][CH2:24][N:25]([CH3:26])[CH3:27])=[O:20]

Participants

4

Reactant 1

HCID 154318761-Methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-N-[3-(dimethylamino)propyl]-1H-pyrrole-2-carboxamide

Product 1

HCID 109925971-Methyl-4-{[(1-methyl-4-amino-1H-pyrrol-2-yl)carbonyl]amino}-N-[3-(dimethylamino)propyl]-1H-pyrrole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-N-[3-(dimethylamino)propyl]-1H-pyrrole-2-carboxamide (59 mg, 0.156 mmol; see Preparation 2(ii) above) was suspended in methanol (25 mL) to which Pd/C-10% (59 mg) was added at 0° C. under a nitrogen with stirring. The reaction mixture was hydrogenated for 3 h at room temperature and atmospheric pressure. The catalyst was removed over kieselguhr and methanol was removed under reduced pressure to give the amine, which was dissolved in DMF (1.5 mL, dry) and used without further purification.

Workup

  1. additionwas added at 0° C. under a nitrogen
  2. customThe catalyst was removed over kieselguhr and methanol
  3. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-28f58b909b3242f5a6628a2e7f23197e
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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