HCID 57845567, compound → HCID 57845562, compound

HRID 734630Notes

Reaction equation

HRID 734630 reaction equation
[NH2:1][C:2]1[N:3]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[C:6]=1[C:7](=[O:9])[NH2:8].[H][H]>[Pd].CO>[NH2:1][C:2]1[N:3]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:4]=[C:5]([C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)[C:6]=1[C:7](=[O:9])[NH2:8]

Participants

5

Reactant 2

HCID 57845567HCID 57845567, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57845562HCID 57845562, compoundYield 105.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.075 g (0.216 mmol) of tert-butyl 2-amino-3-carbamoyl-4-(4-nitrophenyl)-pyrrole-1-carboxylate is added at a temperature in the region of 25° C. to a suspension of 0.008 g (0.0076 mmol) of 10% palladium on carbon in 12 cm3 of methanol. After hydrogenating for 17 hours in an autoclave under 3 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 0.072 g of tert-butyl 2-amino-4-(4-aminophenyl)-3-carbamoylpyrrole-1-carboxylate, in the form of a yellow solid; 1H NMR (400 MHz, (CD3)2SO, —δ in ppm); 1.55 (s: 9H); from 4.80 to 5.35 (very broad m: 1H); 5.22 (broad s 2H); 6.32 (s: 1H); from 6.40 to 6.85 (very broad m: 1H); 6.60 (broad d, J=8.5 Hz: 2H); 6.99 (broad d, J=8.5 Hz: 2H); 7.01 (broad s: 2H).

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-f2d4d0df548e4b3e9c2eea1ae683ab44
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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