Hydrogen Peroxide → HCID 67141825, compound

HRID 1445086Notes

Reaction equation

HRID 1445086 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][CH3:27])=[C:8]1[CH3:28])[CH:5]=[CH2:6].S([O-])([O-])(=[O:31])=S.[Na+].[Na+].C(=O)([O-])[O-].[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]([CH3:27])=[O:31])=[C:8]1[CH3:28])[CH:5]=[CH2:6]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 67141272HCID 67141272, compound

Product 1

HCID 67141825HCID 67141825, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Hydrogen peroxide (50 wt. %, 100 μl) was added to a solution of 2-(1-allyl-2-methyl-3-methylsulfanyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (45 mg, 0.12 mmol) prepared in Example 631 in acetic acid (3 ml). The reaction mixture was stirred for 30 minutes at room temperature and sodium thiosulfate was added thereto. The reaction mixture was basified with a potassium carbonate solution and then extracted with dichloromethane. The organic layer was dried on anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was dissolved in ethyl ether, saturated with hydrochloric acid gas, and then filtered to give 5.5 mg of the titled compound as a white solid.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in ethyl ether, saturated with hydrochloric acid gas
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7584ef63374f43a99caeaab0f8d2534e
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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