Hydrochloric Acid → HCID 45381083, compound

HRID 1027858Notes

Reaction equation

HRID 1027858 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:18][CH3:19])(=[N:11]C(=O)C(F)(F)F)=[O:10])=[CH:5][CH:4]=1.Cl[C:21]1[N:26]=[C:25]([NH:27][C@H:28]([CH3:33])[C:29]([CH3:32])([OH:31])[CH3:30])[C:24]([C:34]([F:37])([F:36])[F:35])=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(#N)C.[Cl-].[Na+].CO>[CH2:18]([S:9]([C:6]1[CH:5]=[CH:4][C:3]([NH:2][C:21]2[N:26]=[C:25]([NH:27][C@H:28]([CH3:33])[C:29]([OH:31])([CH3:30])[CH3:32])[C:24]([C:34]([F:37])([F:35])[F:36])=[CH:23][N:22]=2)=[CH:8][CH:7]=1)(=[NH:11])=[O:10])[CH3:19]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 58467957HCID 58467957, compoundHCID 58533491HCID 58533491, compound

Product 1

HCID 45381083HCID 45381083, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 5234Sodium ChlorideSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

0.36 ml of 4N solution of hydrogen chloride in dioxane was added to 400 mg (1.43 mmol) of (RS)-S-(4-aminophenyl)-S-ethyl-N-(trifluoroacetyl)sulfoximide and 405 mg (1.43 mmol) of (R)-3-(2-chloro-5-trifluoromethyl-pyrimidin-4-ylamino)-2-methyl-butan-2-ol in 7.0 ml acetonitrile and stirred for 4.5 hours at 60° C. The mixture was evaporated to dryness. 25.0 ml methanol and 788 mg (5.70 mmol) of potassium carbonate were added and it was stirred for one hour at room temperature. It was diluted with saturated sodium chloride solution and was extracted with ethyl acetate (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. 620 mg (1.43 mmol) of the raw product was obtained.

Workup

  1. customThe mixture was evaporated to dryness
  2. stirringit was stirred for one hour at room temperature
  3. extractionwas extracted with ethyl acetate (2×)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9e2d53c5cfa7480394e1028c73c9f996
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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