Hydroxylamine → HCID 178448435, compound

HRID 1966759Notes

Reaction equation

HRID 1966759 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:29]=[CH:28][C:11]3[N:12]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:13]([C:15]4[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=4[C:17]#[N:18])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1.[NH2:30][OH:31]>CCO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:29]=[CH:28][C:11]3[N:12]([C:24]([CH3:25])([CH3:26])[CH3:27])[C:13]([C:15]4[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=4[C:17]([NH:30][OH:31])=[NH:18])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58542037HCID 58542037, compound

Product 1

HCID 178448435HCID 178448435, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of 2-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-fluoro-benzonitrile (500 mg, 1.29 mmol) in EtOH (8 mL) is added hydroxylamine 50% aqueous solution (1.71 mL, 25.88 mmol) at room temperature. The solution is stirred at 75° C. for 18 hours. The reaction mixture is cooled to room temperature and the ethanol removed in vacuo. Water (30 mL) is added to the reaction mixture and the resultant precipitate is filtered and washed with 10% EtOAc/heptane (10 mL) to afford 2-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-fluoro-N-hydroxy-benzamidine (485 mg, 88%).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe ethanol removed in vacuo
  3. additionWater (30 mL) is added to the reaction mixture
  4. filtrationthe resultant precipitate is filtered
  5. washwashed with 10% EtOAc/heptane (10 mL)

Sources & evidence

ORD record
ord-1c167bd3fa9440df8ef12addda3ceed5
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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