Ethanol → HCID 10218201, compound

HRID 644803Notes

Reaction equation

HRID 644803 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]([C:10]([NH:12][C:13]3[CH:17]=[C:16]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[O:19])[N:15]([CH3:27])[CH:14]=3)=[O:11])=[CH:8][C:7]([NH:28][C:29]([C:31]3[N:32]([CH3:39])[CH:33]=[C:34]([N+:36]([O-])=O)[CH:35]=3)=[O:30])=[CH:6]2)[CH2:3][CH2:2]1.[CH2:40]([OH:42])C>[Pd]>[CH:1]1([CH2:4][N:5]2[C:9]([C:10]([NH:12][C:13]3[CH:17]=[C:16]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[O:19])[N:15]([CH3:27])[CH:14]=3)=[O:11])=[CH:8][C:7]([NH:28][C:29]([C:31]3[N:32]([CH3:39])[CH:33]=[C:34]([NH:36][CH:40]=[O:42])[CH:35]=3)=[O:30])=[CH:6]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 702EthanolHCID 68679548HCID 68679548, compound

Product 1

HCID 10218201HCID 10218201, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

N-[1-(Cyclopropylmethyl)-5-({[5-({[3-(dimethylamino)propyl]amino}-carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1H-pyrrol-3-yl]-1-methyl-4-nitro-1H-pyrrole-2-carboxamide (100 mg, 0.186 mmol; see step (iv) above) was dissolved in ethanol (25 mL) to which Pd/C-10% (78 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. Ethyl formate was added to the ethanolic solution of the amine and 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 pale yellow solid (52 mg, 42% yield) after freeze drying with no distinct melting point.

Workup

  1. additionwas added at 0° C. under N2
  2. customThe catalyst was removed over Kieselguhr
  3. additionEthyl formate was added to the ethanolic solution of the amine
  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

Sources & evidence

ORD record
ord-65f4e1437c5f48a9867aeb41aace96ad
Source dataset
uspto-grants-2010_04
Patent number
US07700765B2

Reaction notes

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