Methanol → N-(1H-indazol-4-yl)-3-(2-methyl-6-(methylsulfinyl)pyrimidin-4-yl)quinoxalin-2-amine

HRID 1621653Notes

Reaction equation

HRID 1621653 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([NH:10][C:11]3[C:20]([C:21]4[CH:26]=[C:25]([S:27][CH3:28])[N:24]=[C:23]([CH3:29])[N:22]=4)=[N:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.C1C=C(Cl)C=C(C(OO)=[O:38])C=1.CO>C(Cl)Cl.CN(C=O)C.C([O-])(O)=O.[Na+].C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[C:5]([NH:10][C:11]3[C:20]([C:21]4[CH:26]=[C:25]([S:27]([CH3:28])=[O:38])[N:24]=[C:23]([CH3:29])[N:22]=4)=[N:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

7

Reactant 3

HCID 887MethanolHCID 70297m-Chloroperbenzoic acidHCID 66611881N-(1H-indazol-4-yl)-3-(2-methyl-6-(methylthio)pyrimidin-4-yl)quinoxalin-2-amine

Product 1

HCID 66610812N-(1H-indazol-4-yl)-3-(2-methyl-6-(methylsulfinyl)pyrimidin-4-yl)quinoxalin-2-amineYield 23.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 50 mL round-bottomed flask was charged with N-(1H-indazol-4-yl)-3-(2-methyl-6-(methylthio)pyrimidin-4-yl)quinoxalin-2-amine (150 mg, 0.375 mmol) in DCM-DMF(5:1, 6 mL). mCPBA (130 mg, 0.751 mmol, Aldrich) was added to this solution at 0° C., the mixture was stirred at 0° C. for 2 h, then warmed to room temperature and diluted with saturated NaHCO3. The aqueous layer was extracted with DCM (3×), and the combined organic extracts were washed with brine, dried over MgSO4, and concentrated in vacuo. The crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g) eluting with a gradient of 2% to 10% 2M NH3.MeOH in DCM to give N-(1H-indazol-4-yl)-3-(2-methyl-6-(methylsulfinyl)pyrimidin-4-yl)quinoxalin-2-amine (36 mg, 0.087 mmol, 23% yield) as an orange solid. m/z (ESI, +ve ion) 416 (M+H)+.

Workup

  1. temperaturewarmed to room temperature
  2. extractionThe aqueous layer was extracted with DCM (3×)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g)
  7. washeluting with a gradient of 2% to 10% 2M NH3

Sources & evidence

ORD record
ord-0936f93d08a94994b292ba34769621a6
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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