m-Chloroperbenzoic acid → 2-((2-Chloro-5-cyano-3-(oxiran-2-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 921902

Reaction equation

HRID 921902 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:18]([CH:19]=[CH2:20])=[CH:17][C:16]([C:21]#[N:22])=[CH:15][C:14]=1[NH:23][C:24]1[N:29]=[C:28]([NH:30][CH:31]2[CH2:33][CH2:32]2)[C:27]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:26]2[N:25]=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[C:18]([CH:19]2[CH2:20][O:9]2)=[CH:17][C:16]([C:21]#[N:22])=[CH:15][C:14]=1[NH:23][C:24]1[N:29]=[C:28]([NH:30][CH:31]2[CH2:32][CH2:33]2)[C:27]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:26]2[N:25]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 867086492-((2-Chloro-5-cyano-3-vinylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Product 1

HCID 899229452-((2-Chloro-5-cyano-3-(oxiran-2-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrileYield 82.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Added MCPBA (70% wet, 3330 mg, 13.5 mmol) in portions to an ice-cooled suspension of 2-((2-chloro-5-cyano-3-vinylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 399)(339 mg, 0.900 mmol) in CHCl3 (90 mL). The bath was removed and the reaction was left stirring at room temperature for 2 days. This was diluted with CHCl3 and washed with 5% aq. NaHSO3 solution and then 3 times 1 N Na2CO3 solution. After drying with sodium sulfate, the solvent was removed and radial silica gel chromatography eluting with DCM containing 0 to 10% EtOAc afforded 2-((2-chloro-5-cyano-3-(oxiran-2-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (293 mg) as a white solid.

Workup

  1. temperaturecooled
  2. customThe bath was removed
  3. waitthe reaction was left
  4. additionThis was diluted with CHCl3
  5. washwashed with 5% aq. NaHSO3 solution
  6. dry with materialAfter drying with sodium sulfate
  7. customthe solvent was removed
  8. washradial silica gel chromatography eluting with DCM containing 0 to 10% EtOAc

Sources & evidence

ORD record
ord-7d97d56a8d374dccb3dbeb7957ee56b8
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Linked notes

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