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

HRID 1027849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1027849
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]([CH:42]2[CH2:44][CH2:43]2)(=[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]([CH:42]3[CH2:44][CH2:43]3)(=[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

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 468994684-[(1R,2R)-2-benzyloxy-1-methyl-propoxy]-2-chloro-5-(trifluoromethyl)pyrimidineHCID 58533486N-[(R)-(4-Aminophenyl)(cyclopropyl)oxidosulphanylidene]-2,2,2-trifluoroacetamide

Produkt 1

HCID 58533490(RS)-S-(4-{[4-{[(1R,2R)-2-(Benzyloxy)-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-S-cyclopropyl-N-(trifluoroacetyl)sulfoximideAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

0.96 ml of 4N solution of hydrogen chloride in dioxane was added to 1.39 g (3.85 mmol) of 4-((1R,2R)-2-benzyloxy-1-methyl-propoxy)-2-chloro-5-trifluoromethyl-pyrimidine and 1.35 g (4.62 mmol) (RS)-S-(4-aminophenyl)-S-cyclopropyl-N-(trifluoroacetyl)sulfoximide in 18.8 ml acetonitrile and stirred for 5 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 obtained was purified chromatographically (hexane/ethyl acetate 4:1). 1.32 g (2.14 mmol, yield: 56%) of the product was obtained.

Aufarbeitung

  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 obtained
  7. customwas purified chromatographically (hexane/ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-3c8869aad46147a89521cd34d8bc92fe
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735412B2

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