HCID 69056237, compound → HCID 69059637, compound

HRID 734639Notes

Reaction equation

HRID 734639 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8]([NH:10][C:11]2[NH:12][CH:13]=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)[C:15]=2[C:16]([NH2:18])=[O:17])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].CO>[CH:1]1([CH2:6][CH2:7][C:8]([NH:10][C:11]2[NH:12][CH:13]=[C:14]([C:19]3[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=3)[C:15]=2[C:16]([NH2:18])=[O:17])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 69056237HCID 69056237, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69059637HCID 69059637, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.210 g (0.56 mmol) of 2-(3-cyclopentylpropionylamino)-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide is added at a temperature in the region of 25° C. to a suspension of 0.055 g (0.0051 mmol) of 10% palladium on carbon in 25 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 0.151 g of 2-(3-cyclopentylpropionylamino)-4-(4-aminophenyl)-1H-pyrrole-3-carboxamide, in the form of a brown powder. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm) 1.09 (m, 2H); from 1.39 to 1.84 (m, 9H); 2.39 (t, J=8.0 Hz, 2H); 5.14 (broad s, 2H); from 6.20 to 7.50 (very broad m, 2H); 6.23 (d, J=2.5 Hz, 1H); 6.59 (d, J=8.5 Hz, 2H); 6.99 (d, J=8.5 Hz, 2H); 10.9 (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-1041bad99b3a4501aa46e7ac44e285e4
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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