HCID 69357050, compound → HCID 45095360, compound

HRID 852603Notes

Reaction equation

HRID 852603 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[C:9]([C:15]([O:17][CH3:18])=[O:16])[CH:10]=[C:11]([N+:12]([O-])=O)[C:6]=2[N:5]=[CH:4]1)[CH3:2]>CO.O.[Pd]>[NH2:12][C:11]1[C:6]2[N:5]=[CH:4][N:3]([CH2:1][CH3:2])[C:7]=2[CH:8]=[C:9]([C:15]([O:17][CH3:18])=[O:16])[CH:10]=1

Participants

5

Reactant 1

HCID 69357050HCID 69357050, compound

Product 1

HCID 45095360HCID 45095360, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 1-ethyl-4-nitro-1H-benzimidazole-6-carboxylate (D206) (700 mg, 2.81 mmol, 1 equiv) in MeOH (50 ml) and H2O (5 ml) was added 10% palladium on charcoal (50% wet, 400 mg, 28% w/w) and NH4COOH (1.77 g, 28.1 mmol, 10 equiv) and the resulting mixture was stirred at 70° C. for 30 min then cooled to room temperature. The catalyst was filtered off through a pad of celite and most of the MeOH was removed in vacuo. The residue was diluted with AcOEt and the organic layer was washed with a saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo to give methyl 4-amino-1-ethyl-1H-benzimidazole-6-carboxylate (D207) (500 mg, 81%) as a white solid which was used in the next step without further purification. [M+H]+=220.2, RT=2.17 min.

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationThe catalyst was filtered off through a pad of celite and most of the MeOH
  3. customwas removed in vacuo
  4. additionThe residue was diluted with AcOEt
  5. washthe organic layer was washed with a saturated aqueous NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12f02958615c4e42ae0c6e21ced57537
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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