Ammonium formate → Ethyl 3-{5-[(4-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

HRID 1676043Notes

Reaction equation

HRID 1676043 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([C:8]([NH:10][C:11]2[CH:32]=[CH:31][C:14]3[N:15]([CH:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:16]=[N:17][C:13]=3[CH:12]=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:34]=[CH:33][C:7]([C:8]([NH:10][C:11]2[CH:32]=[CH:31][C:14]3[N:15]([CH:18]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:16]=[N:17][C:13]=3[CH:12]=2)=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 58653626Ethyl 3-{5-[(4-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Product 1

HCID 58653682Ethyl 3-{5-[(4-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-{5-[(4-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (297 mg, 648 μmol) in a mixture of ethanol and water (4:1, 10 mL), was added palladium on carbon (60 mg, 10% w/w Pd) and ammonium formate (245 mg, 3.89 mmol). The resulting 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 to dryness, to afford the crude title compound, which was used directly without further purification, [LCMS (Method A, Mobile Phase I) RT=4.04 min, MH+ 430].

Workup

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

Sources & evidence

ORD record
ord-cdd32f6c3a8b4e89aaf060a81caa78a8
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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