Hydrochloric Acid → (RS)-S-(4-{[4-{[(1R,2R)-2-(Benzyloxy)-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-S-methyl-N-(trifluoroacetyl)sulfoximide

HRID 1027852Notes

Reaction equation

HRID 1027852 reaction equation
Cl.[CH2:2]([O:9][C@H:10]([CH3:25])[C@@H:11]([CH3:24])[O:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15](Cl)[N:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([CH3:42])(=[N:35][C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])=[O:34])=[CH:29][CH:28]=1>O1CCOCC1.C(#N)C.C(OCC)(=O)C>[CH2:2]([O:9][C@H:10]([CH3:25])[C@H:11]([O:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([S:33]([CH3:42])(=[N:35][C:36](=[O:41])[C:37]([F:40])([F:38])[F:39])=[O:34])=[CH:31][CH:32]=2)[N:14]=1)[CH3:24])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 468994684-[(1R,2R)-2-benzyloxy-1-methyl-propoxy]-2-chloro-5-(trifluoromethyl)pyrimidineHCID 58533493(RS)-S-(4-Aminophenyl)-S-methyl-N-(trifluoroacetyl)sulfoximide

Product 1

HCID 58533492(RS)-S-(4-{[4-{[(1R,2R)-2-(Benzyloxy)-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-S-methyl-N-(trifluoroacetyl)sulfoximideYield 77%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

0.97 ml of 4N solution of hydrogen chloride in dioxane was added to 1.40 g (3.88 mmol) of 4-((1R,2R)-2-benzyloxy-1-methyl-propoxy)-2-chloro-5-trifluoromethyl-pyrimidine and 1.20 g (4.51 mmol) (RS)-S-(4-aminophenyl)-S-methyl-N-(trifluoroacetyl)sulfoximide in 19.0 ml acetonitrile and was then stirred for 6 hours at 80° C. After cooling, the mixture was diluted with ethyl acetate and washed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated by evaporation. The residue is obtained was purified chromatographically (hexane/ethyl acetate 1:1). 1.76 g (2.98 mmol, yield: 77%) of the product was obtained.

Workup

  1. temperatureAfter cooling
  2. washwashed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe residue is obtained
  7. customwas purified chromatographically (hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-5152ab0f9d5f4ebeabb3e3226b8e7777
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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