Ammonium formate → 3-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester

HRID 2362197Notes

Reaction equation

HRID 2362197 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][CH2:6][C:7]1[N:8]([C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:29])[NH2:28])=[CH:23][C:22]=2[CH3:30])[C:9](C2C=CC=CC=2[N+]([O-])=O)=[CH:10][CH:11]=1)[CH3:2].C([O-])=O.[NH4+:35]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][CH2:6][C:7]1[N:8]([C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:29])[NH2:28])=[CH:23][C:22]=2[CH3:30])[C:9]([C:21]2[CH:26]=[CH:25][C:24]([NH2:35])=[CH:23][CH:22]=2)=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 671789523-[1-(4-carbamoyl-2-methyl-phenyl)-5-(nitro-phenyl)-1H-pyrrole-2-yl]-propanoic acid ethyl ester

Product 1

HCID 583056233-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-[1-(4-carbamoyl-2-methyl-phenyl)-5-(nitro-phenyl)-1H-pyrrole-2-yl]-propanoic acid ethyl ester (83 mg, 0.2 mmol) was dissolved in 2 mL methanol under an inert atmosphere of nitrogen. To this solution was added ammonium formate (117 mg, 1.8 mmol) and 10% Pd/C (10 mg). After 24 hrs, the reaction mixture was filtered using celite, rinsed with MeOH and concentrated in vacuo. The residue was diluted with acetone, filtered and the filtrate concentrated in vacuo to give the crude product, which was purified using preparative TLC (solvent: 5% IPA/CH2Cl2). The band corresponding to 3-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]-propanoic acid ethyl ester (Rf=0.6) was isolated and dried under high vacuum (36 mg, 77%, light orange hydroscopic powder).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washrinsed with MeOH
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with acetone
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customto give the crude product, which
  8. customwas purified

Sources & evidence

ORD record
ord-e09a5005b4cf4aaa83df110db047f425
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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