Ammonium formate → Ethyl 3-{5-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

HRID 1676052Notes

Reaction equation

HRID 1676052 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][CH:32]=[CH:31][C:5]=1[C:6]([NH:8][C:9]1[CH:30]=[CH:29][C:12]2[N:13]([CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:14]=[N:15][C:11]=2[CH:10]=1)=[O:7])([O-])=O.C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[NH2:1][C:4]1[CH:34]=[CH:33][CH:32]=[CH:31][C:5]=1[C:6]([NH:8][C:9]1[CH:30]=[CH:29][C:12]2[N:13]([CH:16]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:14]=[N:15][C:11]=2[CH:10]=1)=[O:7]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 58653693Ethyl 3-{5-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Product 1

HCID 58653637Ethyl 3-{5-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-{5-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (30 mg, 66 μmol) in a mixture of ethanol and water (4:1, 5 mL), was added palladium on carbon (6.0 mg, 10% w/w Pd) and ammonium formate (20 mg, 317 μmol). The suspension was heated to reflux for 3 hours, 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), 8.48 (s, 1H), 8.06 (s, 1H), 7.64 (dd, J=7.69, 1.46, 1H), 7.50-7.35 (br, 7H), 7.28-7.24 (m, 1H), 6.82 (dd, J=8.42, 0.73 1H), 6.74-6.70 (m, 1H), 6.18 (dd, J=9.52, 5.86, 1H), 4.09 (1, J=7.32, 2H), 3.66 (dd, J=16.11, 9.52, 1H), 3.51 (dd, J=16.11, 5.86, 1H), 1.13 (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-30e637e465ed4431b57ce4bd6dc4be8b
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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