Water → HCID 66691627, compound

HRID 1773635Notes

Reaction equation

HRID 1773635 reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[N:17]=[C:18](SC)[CH:19]=[C:20]([NH:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])[C:15]4=[N:14][CH:13]=3)=[CH:8][C:7]=2[CH3:29])[CH2:3][CH2:2]1.O[O:32][S:33]([O-:35])=O.[K+].O.[CH3:38]N(C)C=O>>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[N:17]=[C:18]([S:33]([CH3:38])(=[O:35])=[O:32])[CH:19]=[C:20]([NH:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])[C:15]4=[N:14][CH:13]=3)=[CH:8][C:7]=2[CH3:29])[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 23707502Potassium hydroxy sulfiteHCID 56928279HCID 56928279, compound

Product 1

HCID 66691627HCID 66691627, compoundYield 39%

Conditions

Temperature
23 °C

Procedure

To a solution of 38.7 mg (91 μmol) N-cyclopropyl-4-{8-[(2-hydroxy-2-methylpropyl)amino]-6-(methylsulfanyl)imidazo[1,2-b]pyridazin-3-yl}-2-methylbenzamide which was prepared according to intermediate example 15 in 1.2 mL N,N-dimethylformamide were added 168 mg Oxone and the mixture was stirred at 23° C. for 2.5 days. Water was added and the mixture was extracted with dichloromethane. The organic phase was washed with water and dried over sodium sulfate. After filtration and removal of solvent the residue was purified by chromatography to give 18.5 mg (39%) of the title compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and removal of solvent the residue
  5. customwas purified by chromatography

Sources & evidence

ORD record
ord-e515d54dc89a4cb58ce6c19745a5769e
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

Loading…