Hydrogen Peroxide → 3-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzamide

HRID 1966745Notes

Reaction equation

HRID 1966745 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=4[N:23]4[CH:27]=[N:26][CH:25]=[N:24]4)[C:18]#[N:19])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1.[NH4+].[OH-:35].OO>CO.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:28]([CH3:29])([CH3:30])[CH3:31])[C:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=4[N:23]4[CH:27]=[N:26][CH:25]=[N:24]4)[C:18]([NH2:19])=[O:35])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14923Ammonium HydroxideHCID 532376053-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile

Product 1

HCID 585418963-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzamideYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask is added 3-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile (Example 7) (200 mg, 0.46 mmol) in MeOH (5 mL), followed by the addition of NH4OH (2 mL) and H2O2 (1 mL) (30% in water). The reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with EtOAc (20 mL), washed with water (10 mL), brine (5 mL), dried under anhydrous Na2SO4 (500 mg), filtered and concentrated. The residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (89 mg, 42%) as a white solid. LCMS (ESMS): m/z 454.73 (M++1)

Workup

  1. washwashed with water (10 mL), brine (5 mL)
  2. customdried under anhydrous Na2SO4 (500 mg)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-b5fe16b71efe4168b37d27fb2fadc0e6
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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