HCID 69055710, compound → HCID 69059862, compound

HRID 734648Notes

Reaction equation

HRID 734648 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:21]([NH2:23])=[O:22])=[C:12]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[NH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]([C:21]([NH2:23])=[O:22])=[C:12]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[NH:13][CH:14]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 69055710HCID 69055710, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69059862HCID 69059862, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.115 g (0.362 mmol) of 4-(4-nitrophenyl)-2-(3-ethylureido)-1H-pyrrole-3-carboxamide is added at a temperature in the region of 25° C. to a suspension of 0.067 g (0.0636 mmol) of 10% palladium on carbon in 15 cm3 of methanol. After hydrogenating for 2.5 hours in an autoclave under 2 bar of hydrogen, at a temperature in the region of 25° C., the reaction mixture is filtered, the catalyst is rinsed with three times 5 cm3 of methanol and then the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) to give 0.056 g of 4-(4-aminophenyl)-2-(3-ethylureido)-1H-pyrrole-3-carboxamide, in the form of an orange solid; ES+: m/z=289 (MH+).

Workup

  1. filtrationthe reaction mixture is filtered
  2. washthe catalyst is rinsed with three times 5 cm3 of methanol
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-41d5af60fa134c6a96bccd5341ecec0f
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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