Ammonium formate → 3-{6-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

HRID 1676068Notes

Reaction equation

HRID 1676068 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:10]=[CH:11][C:12]2[N:16]=[CH:15][N:14]([CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18][C:19]([O:21]CC)=[O:20])[C:13]=2[CH:30]=1)=[O:7])([O-:3])=[O:2].C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[N+:1]([C:4]1[CH:34]=[CH:33][CH:32]=[CH:31][C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[CH:15][N:14]([CH:17]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:18][C:19]([OH:21])=[O:20])[C:13]=2[CH:30]=1)=[O:7])([O-:3])=[O:2].[NH2:1][C:4]1[CH:34]=[CH:33][CH:32]=[CH:31][C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[CH:15][N:14]([CH:17]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:18][C:19]([OH:21])=[O:20])[C:13]=2[CH:30]=1)=[O:7]

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 58653654Ethyl 3-{6-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Product 2

HCID 116110403-{6-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acidHCID 586536613-{6-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-{6-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (24 mg, 52 μmol) in a mixture of ethanol and water (5:1, 6 mL), was added palladium on carbon (50 mg, 10% w/w Pd) and ammonium formate (17 mg, 270 μmol). The suspension was heated to reflux for 2 hours, cooled to room temperature, filtered through a pad of Celite® and the filtrate was evaporated in vacuo. The residue was taken up in hydrochloric acid (20 mL of a 5N solution) was stirred at room temperature for 72 hours, evaporated in vacuo, and the residue was purified by RP-HPLC to afford the title compounds 3-{6-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid, [LCMS (Method A, Mobile Phase II) RT=3.65 min, MH+ 401], and 3-{6-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid, [LCMS (Method A, Mobile Phase II) RT=3.58 min, MH+ 431].

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
  5. customevaporated in vacuo
  6. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-f84f1f6fd0ee42278a74dae6c6e375df
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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