1-Methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-N-[2-(4-morpholinyl)ethyl]-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 907362Notes

Reaction equation

HRID 907362 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]N1CCOCC1)=[O:20]>CO.[Pd]>[NH2:15][C:13]1[CH:14]=[C:10]([C:8]([NH:7][C:5]2[CH:4]=[C:3]([C:19]([NH:21][CH2:22][CH2:23][CH2:1][N:2]([CH3:6])[CH3:3])=[O:20])[N:2]([CH3:1])[CH:6]=2)=[O:9])[N:11]([CH3:18])[CH:12]=1

Participants

4

Reactant 1

HCID 108623481-Methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-N-[2-(4-morpholinyl)ethyl]-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-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-carboxamide (150 mg, 0.371 mmol; see step (ii) above) was suspended in methanol (25 mL) to which Pd/C-10% (108 mg) was added at 0° C. under a nitrogen with stirring. The reaction mixture was hydrogenated for 5 h at room temperature and atmospheric pressure. The catalyst was removed over Kieselguhr and methanol was removed under reduced pressure to give the title compound, which was 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-88d328a4c09344b7bc1b6396f39a2e59
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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