HCID 57756882, compound → HCID 57756892, compound

HRID 227669Notes

Reaction equation

HRID 227669 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)=[C:11]([C:14]([NH2:16])=[O:15])[NH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[C:11]([C:14]([NH2:16])=[O:15])[NH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 57756882HCID 57756882, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57756892HCID 57756892, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 0.024 g (0.222 mmol) of 10% palladium-on-charcoal in 63 cm3 of methanol is added, at a temperature in the region of 20° C., 0.331 g (0.956 mmol) of 4-tert-butyloxycarbonylamino-3-(4-nitrophenyl)-1H-pyrrole-2-carboxamide. After hydrogenating for 5 hours in an autoclave under 4 bar of hydrogen, at a temperature in the region of 40° C., the reaction mixture is filtered. The catalyst is rinsed with twice 15 cm3 of methanol and the filtrate is then concentrated to dryness under reduced pressure (2.7 kPa) to give 0.3 g of 4-tert-butyloxycarbonylamino-3-(4-aminophenyl)-1H-pyrrole-2-carboxamide in the form of a white solid melting at about 142° C.; EI: m/z=316 M+; m/z=260 [M-tBu]+; m/z=243 [M-OtBu]+; m/z=199 [243-CONH2]+; m/z=57: [tBu]+ base peak.

Workup

  1. filtrationthe reaction mixture is filtered
  2. washThe catalyst is rinsed with twice 15 cm3 of methanol
  3. concentrationthe filtrate is then concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-e90493ea6b544f308ad68629e03e3587
Source dataset
uspto-grants-2009_07
Patent number
US07560571B2

Reaction notes

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