Water → HCID 58653671, compound

HRID 1676087Notes

Reaction equation

HRID 1676087 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH:7]([N:13]2[C:17]3[CH:18]=[CH:19][C:20]([N+:22]([O-])=O)=[CH:21][C:16]=3[N:15]=[CH:14]2)[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:3][CH:2]=1.C([O-])=O.[NH4+].O>C(O)C.[Pd]>[NH2:22][C:20]1[CH:19]=[CH:18][C:17]2[N:13]([CH:7]([C:4]3[CH:5]=[CH:6][C:1]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:2][CH:3]=3)[CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:14]=[N:15][C:16]=2[CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 58653692HCID 58653692, compound

Product 1

HCID 58653671HCID 58653671, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl 3-(1,1′-biphenyl)-4-yl-3-(5-nitro-1H-benzimidazol-1-yl)propanoate (47 mg, 117 μmol) in ethanol (2 mL) was added palladium on carbon (9.0 mg, 10% active Pd), ammonium formate (37 mg, 587 μmol) and water (0.5 mL). The solution was heated at reflux for 4 hours, the cooled to room temperature, and filtered through Celite®. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (97:3) to afford the title compound, [LCMS (Method B, Mobile Phase I) RT=2.26 min, MH+ 372].

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 4 hours
  3. filtrationfiltered through Celite®
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was purified by flash column chromatography on silica gel
  6. washeluting with a mixture of dichloromethane and methanol (97:3)

Sources & evidence

ORD record
ord-497afc7d9745493ba1e23526850153ad
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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