Potassium peroxymonosulphate → HCID 49868875, compound

HRID 570939Notes

Reaction equation

HRID 570939 reaction equation
[CH3:1][S:2][CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH:11]=[N:12][C:13]([C:14]3[O:15][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:17][N:18]=3)=[C:7]2[N:6]=[N:5]1.S([O-])(O[O-])(=O)=[O:26].[K+].[K+].OOS([O-])=O.[K+]>CN(C=O)C.O>[CH3:1][S:2]([CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH:11]=[N:12][C:13]([C:14]3[O:15][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:17][N:18]=3)=[C:7]2[N:6]=[N:5]1)=[O:26]

Participants

6

Reactant 3

HCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 66831858HCID 66831858, compound

Product 1

HCID 49868875HCID 49868875, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 3-(methylthiomethyl)-8-(5-phenyl-1,3,4-oxadiazol-2-yl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one (0.337 mmol, 115 mg, 1 eq.) in DMF (6 mL) was added potassium peroxymonosulfate (Oxone™) (0.37 mmol, 114 mg, 1.1 eq.) dissolved in water (1.2 mL) drop wise. The formed suspension was stirred at 0° C. and stepwise additions of Oxone™ in water were made until reaction completion. The reaction mixture was filtered and the obtained solid was washed with water, acetonitrile and ether, and dried under vacuum to give the title compound. Yield 90%. δH (DMSO-d6) 9.15 (1H, s), 8.13 (2H, dd, J: 7.96, 2.25), 7.70 (3H, m), 5.67 (1H, d, J: 13.06), 5.52 (1H, d, J: 13.06), 2.81 (3H, s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe obtained solid was washed with water, acetonitrile and ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-73007035acc14c97abcfb0168ee76944
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

Loading…