Water → [6-(2-Cylohexylsulfanyl-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine

HRID 1854604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854604
Cl[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].[CH:27]1([SH:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.O>CC(O)C>[CH:27]1([S:33][C:2]2[O:3][C:4]([C:7]3[N:12]=[C:11]([NH:13][C:14]4[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=4)[CH:10]=[CH:9][CH:8]=3)=[CH:5][N:6]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15290CyclohexanethiolHCID 53311311HCID 53311311, Verbindung

Produkt 1

HCID 53312329[6-(2-Cylohexylsulfanyl-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of [6-(2-chloro-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (50 mg, 0.174 mmol), K2CO3 (72 mg, 0.523 mmol) and cyclohexanethiol (64 μl, 0.523 mmol) in iPrOH (5 ml) were heated to reflux for 18 h. The cooled mixture was treated with water and extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure to a yellow gum. The gum was taken up in a minimum of DCM and precipitated with n-pentane to afford the title compound as a beige solid (45 mg, 71%). 1H NMR (300 MHz, DMSO-d6) δ 9.76 (s, 1H), 8.10 (s, 1H), 7.56-7.78 (m, 4H), 7.17 (d, J=5.9 Hz, 1H), 6.75 (s, 1H), 3.71 (m, 1H), 2.31 (s, 3H), 2.08 (m, 2H), 1.64 (m, 8H). (ESI+) m/z 367 (M+H)+.

Aufarbeitung

  1. temperaturewere heated
  2. temperatureto reflux for 18 h
  3. extractionextracted with DCM
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure to a yellow gum
  7. customprecipitated with n-pentane

Quellen und Nachweise

ORD-Eintrag
ord-5842e570d1754d8080b0cedef6bdc4fc
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962665B2

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