Ammonium formate → Ethyl 3-{6-[(3-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

HRID 1676064Notes

Reaction equation

HRID 1676064 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[CH:16][N:15]([CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:14]=2[CH:31]=1)=[O:8])([O-])=O.C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[CH:16][N:15]([CH:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:14]=2[CH:31]=1)=[O:8]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 58653702Ethyl 3-{6-[(3-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Product 1

HCID 58653689Ethyl 3-{6-[(3-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-{6-[(3-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (231 mg, 504 μmol) in a mixture of ethanol and water (4:1, 10 mL), was added palladium on carbon (46 mg, 10% w/w Pd) and ammonium formate (191 mg, 3.03 mmol). The suspension was heated to reflux for 3 hours, and was then cooled to room temperature, and filtered through a pad of Celite®. The filtrate was evaporated in vacuo to afford the title compound, 1H NMR: (CD3OD), 8.43 (s, 1H), 8.14 (d, J=1.46, 1H), 7.65 (d, J=8.79, 1H), 7.47 (dd, J=8.79, 1.83, 1H), 7.30 (br, 8H), 6.92-6.90 (m, 1H), 6.11 (dd, J=9.52, 6.22, 1H), 4.04 (q, J=7.32, 2H), 3.62 (dd, J=16.11, 9.52, 1H), 3.46 (dd, J=16.11, 6.22, 1H), 1.08 (t, J=7.32, 3H).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered through a pad of Celite®
  4. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-3a835c4549774a6d9a53a9380933651b
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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