Hydroxylamine → HCID 178448433, compound

HRID 1966765Notes

Reaction equation

HRID 1966765 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:28]=[CH:27][C:11]3[N:12]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:13]([C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[C:17]#[N:18])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1.[NH2:29][OH:30]>CCO>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:28]=[CH:27][C:11]3[N:12]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:13]([C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[C:17]([NH:29][OH:30])=[NH:18])=[N:14][C:10]=3[CH:9]=2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58541928HCID 58541928, compound

Product 1

HCID 178448433HCID 178448433, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-benzonitrile (1.1 mg, 2.99 mmol) in EtOH (20 mL) is added hydroxylamine 50% aqueous solution (3.94 mL 59.71 mmol) at room temperature. The solution is stirred at 80° C. for 2 hours. The reaction mixture is cooled to room temperature and the ethanol removed in vacuo. EtOAc (50 mL) is added and the organics washed with H2O then dried (Na2SO4), filtered and concentrated to afford 2-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-N-hydroxy-benzamidine (1.1 g, 92%).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe ethanol removed in vacuo
  3. additionEtOAc (50 mL) is added
  4. washthe organics washed with H2O
  5. dry with materialthen dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-af0aafedc5e34a6ea153bd3358d7f697
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

Loading…