HCID 57845576, compound → 2-acetylamino-4-(6-aminopyridin-3-yl)-1H-pyrrole-3-carboxamide

HRID 734642Notes

Reaction equation

HRID 734642 reaction equation
[C:1]([NH:4][C:5]1[NH:6][CH:7]=[C:8]([C:13]2[CH:14]=[N:15][C:16]([N+:19]([O-])=O)=[CH:17][CH:18]=2)[C:9]=1[C:10]([NH2:12])=[O:11])(=[O:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([NH:4][C:5]1[NH:6][CH:7]=[C:8]([C:13]2[CH:14]=[N:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[C:9]=1[C:10]([NH2:12])=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 57845576HCID 57845576, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 578455742-acetylamino-4-(6-aminopyridin-3-yl)-1H-pyrrole-3-carboxamideYield 81.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.15 g (0.519 mmol) of 2-acetylamino-4-(6-nitropyridin-3-yl)-1H-pyrrole-3-carboxamide is added at a temperature in the region of 25° C. to a suspension of 0.015 g (0.014 mmol) of 10% palladium on carbon in 20 cm3 of methanol. After hydrogenating for 2 hours in an autoclave under 2 bar of hydrogen, at a temperature in the region of 30° C., the reaction mixture is filtered, the catalyst is rinsed with twice 2 cm3 of ethyl ether. After draining and drying, 0.11 g of 2-acetylamino-4-(6-aminopyridin-3-yl)-1H-pyrrole-3-carboxamide is obtained, in the form of a brown solid. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm) 2.13 (s, 3H); 6.01 (broad s, 2H); from 5.50 to 8.85 (very broad m, 2H); 6.35 (d, J=2.5 Hz, 1H); 6.49 (d, J=8.5 Hz, 1H); 7.36 (dd, J=2.5 and 8.5 Hz, 1H); 7.87 (d, J=2.5 Hz, 1H); 10.65 (s, 1H); 11.35 (broad s, 1H).

Workup

  1. filtrationthe reaction mixture is filtered
  2. washthe catalyst is rinsed with twice 2 cm3 of ethyl ether
  3. customdrying

Sources & evidence

ORD record
ord-c0fa67b85e004a3b89c8d977bf861df8
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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