HCID 69060826, compound → HCID 69057492, compound

HRID 734636Notes

Reaction equation

HRID 734636 reaction equation
[C:1]([NH:6][C:7]1[NH:8][CH:9]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[C:11]=1[C:12]([NH2:14])=[O:13])(=[O:5])[CH2:2][CH2:3][CH3:4].[H][H]>[Pd].CO>[C:1]([NH:6][C:7]1[NH:8][CH:9]=[C:10]([C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[C:11]=1[C:12]([NH2:14])=[O:13])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 69060826HCID 69060826, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69057492HCID 69057492, compoundYield 118.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.195 g (0.61 mmol) of 2-butyrylamino-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide is added at a temperature in the region of 25° C. to a suspension of 0.068 g (0.064 mmol) of 10% palladium on carbon in 20 cm3 of methanol. After hydrogenating for 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 twice 10 cm3 of methanol and then the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) to give 0.207 g of 2-butyrylamino-4-(4-aminophenyl)-1H-pyrrole-3-carboxamide, in the form of a cream solid. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm) 0.94 (t, J=7.5 Hz, 3H); 1.63 (m, 2H); 2.37 (t, J=7.5 Hz, 2H); 5.11 (broad s, 2H); from 6.05 to 8.45 (very broad m, 2H); 6.24 (d, J=2.5 Hz, 1H); 6.60 (d, J=8.5 Hz, 2H); 6.99 (d, J=8.5 Hz, 2H); 10.8 (broad s, 1H); 11.3 (broad s, 1H).

Workup

  1. filtrationthe reaction mixture is filtered
  2. washthe catalyst is rinsed with twice 10 cm3 of methanol
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-0e7aa88e09774f1ca334f1f805ad1d89
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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