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-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-carboxamide

HRID 907392Notes

Reaction equation

HRID 907392 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][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[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][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:20]

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 121500711-Methyl-4-{[(1-methyl-4-amino-1H-pyrrol-2-yl)carbonyl]amino}-N-[2-(4-morpholinyl)ethyl]-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 (86 mg, 0.212 mmol; see Preparation 1 (iv) above) was suspended in methanol (25 mL) to which Pd/C-10% (80 mg) was added at 0° C. under nitrogen with stirring. The reaction mixture was hydrogenated for 4 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 mL, dry). The resulting amine was utilised in the next step without purification.

Workup

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

Sources & evidence

ORD record
ord-fe6121e0d1b04e2cbcefee95e30feebd
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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