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

HRID 1676048Notes

Reaction equation

HRID 1676048 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:31]=[CH:30][C:13]2[N:14]([CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:15]=[N:16][C:12]=2[CH:11]=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:31]=[CH:30][C:13]2[N:14]([CH:17]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:15]=[N:16][C:12]=2[CH:11]=1)=[O:8]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 58653703Ethyl 3-{5-[(3-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Product 1

HCID 58653680ethyl 3-{5-[(3-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-{5-[(3-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (190 mg, 415 μmol) in a mixture of ethanol and water (4:1, 10 mL) was added palladium on carbon (38 mg, 10% w/w Pd) and ammonium formate (130 mg, 2.06 mmol). The suspension was heated to reflux for 2 hours, cooled to room temperature and filtered through a pad of Celite®. The filtrate was then evaporated in vacuo to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=3.85 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 then evaporated in vacuo

Sources & evidence

ORD record
ord-a8a7dcc0213b4ab19822f08feb3b1e3e
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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