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Hydrochloric Acid → (RS)-S-(4-{[4-{[(1 R,2R)-2-Hydroxy-1-methylpropyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-S-methylsulfoximide

HRID 1027859
Notes
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Reaction equation

HRID 1027859 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:18])(=[N:11]C(=O)C(F)(F)F)=[O:10])=[CH:5][CH:4]=1.Cl[C:20]1[N:25]=[C:24]([NH:26][C@H:27]([CH3:31])[C@H:28]([OH:30])[CH3:29])[C:23]([C:32]([F:35])([F:34])[F:33])=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(#N)C.[Cl-].[Na+].CO>[OH:30][C@H:28]([CH3:29])[C@H:27]([NH:26][C:24]1[C:23]([C:32]([F:35])([F:34])[F:33])=[CH:22][N:21]=[C:20]([NH:2][C:3]2[CH:4]=[CH:5][C:6]([S:9]([CH3:18])(=[NH:11])=[O:10])=[CH:7][CH:8]=2)[N:25]=1)[CH3:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 58533493(RS)-S-(4-Aminophenyl)-S-methyl-N-(trifluoroacetyl)sulfoximideHCID 59683169(2R,3R)-3-(2-Chloro-5-trifluoromethylpyrimidin-4-ylamino)butan-2-ol

Product 1

HCID 45381084(RS)-S-(4-{[4-{[(1 R,2R)-2-Hydroxy-1-methylpropyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-S-methylsulfoximide
Yield 93.3%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
60 °C

Procedure

0.38 ml of 4N solution of hydrogen chloride in dioxane was added to 399 mg (1.50 mmol) of (RS)-S-(4-aminophenyl)-S-methyl-N-(trifluoroacetyl)sulfoximide and 404 mg (1.50 mmol) of (2R,3R)-3-(2-chloro-5-trifluoromethyl-pyrimidin-4-ylamino)-butan-2-ol in 7.3 ml acetonitrile and stirred for 9 hours at 60° C. The mixture was evaporated to dryness. 32.2 ml methanol and 1040 mg (7.50 mmol) of potassium carbonate were added and it was stirred for 1.5 hours at room temperature. It was diluted with saturated sodium chloride solution and was extracted with ethyl acetate (3×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. 565 mg (1.40 mmol) of the raw product was obtained.

Workup

  1. customThe mixture was evaporated to dryness
  2. stirringit was stirred for 1.5 hours at room temperature
  3. extractionwas extracted with ethyl acetate (3×)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5fae2db7220c44d89dace81b648f3ad5
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08735412B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes