Dimethyl Sulfoxide → Tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(5-methylpyridin-3-ylamino)pyridin-2-ylamino)cyclohexylcarbamate

HRID 1620114Notes

Reaction equation

HRID 1620114 reaction equation
[OH-:1].[Na+].OO.CS(C)=O.[CH3:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]3[NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:20]([F:38])=[CH:19][C:18]=2[C:39]#[N:40])[CH:13]=[N:14][CH:15]=1>O.C(O)C>[NH2:40][C:39]([C:18]1[CH:19]=[C:20]([F:38])[C:21]([NH:23][C@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]2[NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[N:22][C:17]=1[NH:16][C:12]1[CH:13]=[N:14][CH:15]=[C:10]([CH3:9])[CH:11]=1)=[O:1]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86683885Tert-butyl cis-2-(6-(5-methylpyridin-3-ylamino)-5-cyano-3-fluoropyridin-2-ylamino)cyclohexylcarbamate

Product 1

HCID 86683884Tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(5-methylpyridin-3-ylamino)pyridin-2-ylamino)cyclohexylcarbamate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
34 °C

Procedure

A 5N sodium hydroxide aqueous solution (1.18 ml) and 30% hydrogen peroxide solution (0.70 ml) were added to a solution of dimethyl sulfoxide (10 ml) and ethanol (10 ml) containing tert-butyl cis-2-(6-(5-methylpyridin-3-ylamino)-5-cyano-3-fluoropyridin-2-ylamino)cyclohexylcarbamate (520 mg), followed by stirring at 34° C. for 30 minutes. The reaction mixture was cooled to room temperature, and water was added. Solid matter was collected by filtration, dissolved in ethyl acetate and tetrahydrofuran, washed with water and then with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The obtained residue was added to diisopropylether, solid matter was collected by filtration and washed with diisopropylether and hexane, and a light yellow solid of tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(5-methylpyridin-3-ylamino)pyridin-2-ylamino)cyclohexylcarbamate (506 mg) was thus obtained.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationSolid matter was collected by filtration
  3. dissolutiondissolved in ethyl acetate
  4. washtetrahydrofuran, washed with water
  5. dry with materialwith saturated saline, and dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. additionThe obtained residue was added to diisopropylether, solid matter
  8. filtrationwas collected by filtration
  9. washwashed with diisopropylether and hexane

Sources & evidence

ORD record
ord-4bda7150713140c3b1001850c7cfad3f
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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