Cyclohexanol → HCID 25216188, Verbindung

HRID 2382768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382768
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:11]1[N:16]2[N:17]=[C:18]([NH2:20])[N:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH:1]1([O:7][C:11]2[N:16]3[N:17]=[C:18]([NH2:20])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 214644135-Chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Produkt 1

HCID 25216188HCID 25216188, VerbindungAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Cyclohexanol (1.68 mL; 15.84 mmol; 5.0 eq.) was added to a suspension of NaH (152 mg; 3.80 mmol; 1.2 eq.) in THF (6.0 mL) and maintained under inert atmosphere at 0° C. The reaction mixture was brought back to rt and stirred for 1 h before the addition of 5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A4), 534 mg; 3.17 mmol; 1.0 eq.). Reaction mixture was then heated at reflux for 3 h after which time it was quenched by addition of water. It was then extracted with EtOAc, washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (DCM/MeOH, 95:5 to 10:90) gave the title compound as a white solid (590 mg, 80%). HPLC, Rt: 2.18 min. (purity 90.1%). LC/MS, M+(ESI): 233.0.

Aufarbeitung

  1. customwas brought back to rt
  2. customReaction mixture
  3. temperaturewas then heated
  4. temperatureat reflux for 3 h after which time it
  5. customwas quenched by addition of water
  6. extractionIt was then extracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by flash chromatography on silica gel (DCM/MeOH, 95:5 to 10:90)

Quellen und Nachweise

ORD-Eintrag
ord-c19b3b8b4d064619a9c67c3db3309a1f
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263595B2

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