Dimethyl Sulfoxide → HCID 56599958, compound

HRID 340517Notes

Reaction equation

HRID 340517 reaction equation
[OH-:1].[Na+].OO.CS(C)=O.[NH2:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[NH:16][C:17]1[C:24]([F:25])=[CH:23][C:20]([C:21]#[N:22])=[C:19]([NH:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][CH:31]=[N:32]3)[N:18]=1>O.C(O)C>[NH2:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[NH:16][C:17]1[C:24]([F:25])=[CH:23][C:20]([C:21]([NH2:22])=[O:1])=[C:19]([NH:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][CH:31]=[N:32]3)[N:18]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 68618650HCID 68618650, compound

Product 1

HCID 56599958HCID 56599958, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A 5M sodium hydroxide aqueous solution (0.1 ml) and a 30% hydrogen peroxide solution (0.1 ml) were added to a solution of dimethyl sulfoxide (1 ml) and ethanol (0.5 ml) containing 6-(((1R,2S)-2-aminocyclohexyl)amino)-5-fluoro-2-(quinolin-5-ylamino)nicotinonitrile (20 mg), followed by stirring at room temperature for 1 hour. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. 4M hydrogen chloride/1,4-dioxane (0.5 ml) was added to the obtained residue, the resulting precipitate was collected by filtration, and a red solid of 6-(((1R,2S)-2-aminocyclohexyl)amino)-5-fluoro-2-(quinolin-5-ylamino)nicotinamide (12 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. addition4M hydrogen chloride/1,4-dioxane (0.5 ml) was added to the obtained residue
  6. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-131cef240c364cfd85ba0374d850ec36
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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