Water → (3S,6R)-1-(2-Amino-6-chloro-4-pyrimidinyl)-6-methyl-N-phenyl-3-piperidinecarboxamide

HRID 2367416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367416
[CH3:1][C@H:2]1[NH:7][CH2:6][C@@H:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH2:4][CH2:3]1.[Cl:17][C:18]1[CH:23]=[C:22](Cl)[N:21]=[C:20]([NH2:25])[N:19]=1.C([O-])(O)=O.[Na+].O>O1CCOCC1.CCOC(C)=O.ClC1C=C(Cl)N=C(N)N=1>[NH2:25][C:20]1[N:21]=[C:22]([N:7]2[C@H:2]([CH3:1])[CH2:3][CH2:4][C@H:5]([C:8]([NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:9])[CH2:6]2)[CH:23]=[C:18]([Cl:17])[N:19]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 655222-Amino-4,6-dichloropyrimidineHCID 516892Sodium BicarbonateHCID 44174107(3S,6R)-6-Methyl-N-phenyl-3-piperidinecarboxamide

Produkt 1

HCID 58504476(3S,6R)-1-(2-Amino-6-chloro-4-pyrimidinyl)-6-methyl-N-phenyl-3-piperidinecarboxamideAusbeute 116,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 655222-Amino-4,6-dichloropyrimidineKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of (3S,6R)-6-methyl-N-phenyl-3-piperidinecarboxamide (12 g, 55 mmol) in 1,4-dioxane (250 mL) was added 4,6-dichloro-2-pyrimidinamine (8.11 g, 49.5 mmol) and sat. aqueous NaHCO3 (125 mL), and the reaction mixture was then refluxed overnight. The reaction was not completed. The reaction mixture was cooled, added 4,6-dichloro-2-pyrimidinamine (0.9 g, 5.5 mmol), and refluxed overnight. When the reaction was completed, the mixture was cooled down. To the mixture was added about 500 mL of H2O to form a precipitate, and then filtered to obtain a gummy solid. The gummy solid was then dissolved in EtOAc (˜800 mL). The organic solution was washed with water (2×200 mL), brine (200 mL), dried (Na2SO4), filtered, and concentrated in vacuo to afford the crude title compound (20 g). LC-MS (ES) m/z=346 [M+H]+.

Aufarbeitung

  1. temperaturethe reaction mixture was then refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. temperaturerefluxed overnight
  4. temperaturethe mixture was cooled down
  5. customto form a precipitate
  6. filtrationfiltered
  7. customto obtain a gummy solid
  8. washThe organic solution was washed with water (2×200 mL), brine (200 mL)
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7200e9f940fe45cf9c640dce67bd19cf
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

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