Ethanol → HCID 3009898, compound

HRID 644805Notes

Reaction equation

HRID 644805 reaction equation
[CH2:1]([N:6]1[C:10]([C:11]([NH:13][C:14]2[CH:18]=[C:17]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]3)=[O:20])[N:16]([CH3:32])[CH:15]=2)=[O:12])=[CH:9][C:8]([NH:33][C:34]([C:36]2[N:37]([CH3:44])[CH:38]=[C:39]([N+:41]([O-])=O)[CH:40]=2)=[O:35])=[CH:7]1)[CH2:2][CH:3]([CH3:5])[CH3:4].[CH2:45]([OH:47])C>[Pd]>[CH:45]([NH:41][C:39]1[CH:40]=[C:36]([C:34]([NH:33][C:8]2[CH:9]=[C:10]([C:11]([NH:13][C:14]3[CH:18]=[C:17]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)=[O:20])[N:16]([CH3:32])[CH:15]=3)=[O:12])[N:6]([CH2:1][CH2:2][CH:3]([CH3:4])[CH3:5])[CH:7]=2)=[O:35])[N:37]([CH3:44])[CH:38]=1)=[O:47]

Participants

4

Reactant 2

HCID 702EthanolHCID 67183503HCID 67183503, compound

Product 1

HCID 3009898HCID 3009898, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

N-[1-Isopentyl-5-({[1-methyl-5-({[3-(4-methyl-1-piperazinyl)propyl]-amino}carbonyl)-1H-pyrrol-3-yl]amino}carbonyl)-1H-pyrrol-3-yl]-1-methyl-4-nitro-1H-pyrrole-2-carboxamide (120 mg, 0.197 mmol; see step (ii) above) was dissolved in ethanol (20 mL) to which Pd/C-10% (77 mg) was added at 0° C. under N2 with stirring. The reaction mixture was hydrogenated for 3 h at room temperature and atmospheric pressure. The catalyst was removed over Kieselguhr and ethyl formate (20 mL) was added to the ethanolic solution. The reaction mixture was heated under reflux for 48 h. Ethanol and excess ethyl formate were removed under reduced pressure and the crude product was purified by HPLC. The product was obtained as yellow solid with no distinct melting point (75 mg, 53% yield) after freeze-drying.

Workup

  1. additionwas added at 0° C. under N2
  2. customThe catalyst was removed over Kieselguhr and ethyl formate (20 mL)
  3. additionwas added to the ethanolic solution
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for 48 h
  6. customEthanol and excess ethyl formate were removed under reduced pressure
  7. customthe crude product was purified by HPLC
  8. customThe product was obtained as yellow solid with no distinct melting point (75 mg, 53% yield)
  9. customafter freeze-drying

Sources & evidence

ORD record
ord-63b7033ec3ec405b8bfd5a5febc1b9d1
Source dataset
uspto-grants-2010_04
Patent number
US07700765B2

Reaction notes

Loading…