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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1027859
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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 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

Produkt 1

HCID 45381084(RS)-S-(4-{[4-{[(1 R,2R)-2-Hydroxy-1-methylpropyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-S-methylsulfoximide
Ausbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 5234Sodium ChlorideLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5fae2db7220c44d89dace81b648f3ad5
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08735412B2

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