Hydrogen Peroxide → HCID 67142183, compound

HRID 1932373Notes

Reaction equation

HRID 1932373 reaction equation
OO.[ClH:3].[CH2:4]([N:7]1[C:11]2=[C:12]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)[N:13]=[CH:14][CH:15]=[C:10]2[C:9]([S:26]([CH3:28])=[O:27])=[C:8]1[CH3:29])[CH:5]=[CH2:6].C(=O)([O-])[O-:31].[K+].[K+]>C(O)(=O)C>[ClH:3].[CH2:4]([N:7]1[C:11]2=[C:12]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)[N:13]=[CH:14][CH:15]=[C:10]2[C:9]([S:26]([CH3:28])(=[O:31])=[O:27])=[C:8]1[CH3:29])[CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67141825HCID 67141825, compound

Product 1

HCID 67142183HCID 67142183, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Hydrogen peroxide (50 wt. %, 100 μl) was added to a solution of 2-(1-allyl-3-methylsulfinyl-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (30 mg, 0.07 mmol) prepared in Example 632 in acetic acid (3 ml). The reaction mixture was stirred for 1 hour at 60° C., cooled to room temperature, basified with a potassium carbonate solution, and then extracted with dichloromethane. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography. The resulting product was dissolved in ethyl ether, saturated with hydrochloric acid gas, and then filtered to give 8 mg of the titled compound as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography
  6. dissolutionThe resulting product was dissolved in ethyl ether, saturated with hydrochloric acid gas
  7. filtrationfiltered

Sources & evidence

ORD record
ord-c1bf4bddef2549e78917334c024784c2
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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