Hydrogen Peroxide → HCID 118671743, compound

HRID 630496Notes

Reaction equation

HRID 630496 reaction equation
[OH:1]O.[CH3:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][C:13]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:25]([N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)=[O:26])[CH:23]=4)[C:18]([S:33][CH3:34])=[CH:17]3)=[N:14][CH:15]=2)[CH:7]=[CH:6][N:5]=1>C(O)(=O)C.ClCCl>[CH3:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[N:14][C:13]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:25]([N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)=[O:26])[CH:23]=4)[C:18]([S:33]([CH3:34])=[O:1])=[CH:17]3)=[N:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 118666146HCID 118666146, compound

Product 1

HCID 118671743HCID 118671743, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Hydrogen peroxide (30%, 0.4 mL, 3.595 mmol, 4.0 eq) was added to a stirred solution of (1-(5-(2-methylpyridin-4-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone (400 mg, 0.898 mmol, 1.0 eq, synthesized analogously to procedure 1d) in acetic acid (10 mL). The reaction mixture was stirred for 1 h at room temperature and then diluted with dichloromethane (20 mL). The mixture was washed with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate, and evaporated under vacuum. The remnant was purified by preparative silica gel TLC [dichloromethane with 3% methanol]. White solid. Yield: 250 mg

Workup

  1. washThe mixture was washed with saturated sodium hydrogen carbonate solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated under vacuum
  4. customThe remnant was purified by preparative silica gel TLC [dichloromethane with 3% methanol]

Sources & evidence

ORD record
ord-39ce023d2c20445080fe3f711bef3d06
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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