Ammonium formate → Ethyl 3-{6-[(4-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

HRID 1676059Notes

Reaction equation

HRID 1676059 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]3[N:18]=[CH:17][N:16]([CH:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:15]=3[CH:32]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]3[N:18]=[CH:17][N:16]([CH:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:15]=3[CH:32]=2)=[O:9])=[CH:33][CH:34]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 58653684Ethyl 3-{6-[(4-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Product 1

HCID 58653695Ethyl 3-{6-[(4-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-{6-[(4-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (241 mg, 526 μmol) in a mixture of ethanol and water (6:1, 14 mL) was added palladium on carbon (48 mg, 10% w/w Pd) and ammonium formate (200 mg, 3.18 mmol). The suspension was heated to reflux for 2 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, [LCMS (Method A, Mobile Phase II) RT=4.61 min, MH+ 429].

Workup

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

Sources & evidence

ORD record
ord-60667a4e55294b7db89890b5dfd02216
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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