Sodium Bicarbonate → HCID 18436986, Verbindung

HRID 1986930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986930
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[S:21][CH:20]=[CH:19][C:16]=3[NH:17][N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22]C(C)([O-])C.[K+].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[S:21][CH:20]=[CH:19][C:16]=3[N:17]([CH3:22])[N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 184369853-(4-benzyl-piperazin-1-yl)-1H-thieno[3,2-c]pyrazoleHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 18436986HCID 18436986, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

To a stirred solution of 3-(4-benzyl-piperazin-1-yl)-1H-thieno[3,2-c]pyrazole (318.0 g, 1.07 mol) in THF (2.5 L) was added a mixture of potassium t-butoxide (134.4 g, 1.2 mol) in THF (1.5 L) dropwise over a period of 1 hour while keeping the reaction temperature below 25° C. After complete addition, the mixture was cooled to −30° C. and Mel (65.4 mL, 1.05 mol) was added dropwise over a period of 30 minutes. The mixture is then slowly warmed to room temperature overnight. To the reaction mixture is slowly added saturated NaHCO3 (1 L). The solution is then evaporated to remove the THF and the resulting aqueous mixture is taken up in EtOAc and washed with water and brine. The EtOAc extract is dried (Na2SO4), filtered and evaporated. The viscous concentrate is filtered through a silica gel plug with 1:1 EtOAc/heptane and evaporated yielding a viscous oil that is then dried under vacuum where it solidifies and yields 326.03 g (98%) as a 12:1 ratio of regioisomers in favor of the desired product.

Aufarbeitung

  1. customthe reaction temperature below 25° C
  2. additionAfter complete addition
  3. additionMel (65.4 mL, 1.05 mol) was added dropwise over a period of 30 minutes
  4. temperatureThe mixture is then slowly warmed to room temperature overnight
  5. customThe solution is then evaporated
  6. customto remove the THF
  7. washwashed with water and brine
  8. extractionThe EtOAc extract
  9. dry with materialis dried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated
  12. concentrationThe viscous concentrate
  13. filtrationis filtered through a silica gel plug with 1:1 EtOAc/heptane
  14. customevaporated
  15. customyielding a viscous oil that
  16. customis then dried under vacuum where it

Quellen und Nachweise

ORD-Eintrag
ord-87ebfc87105e406fb9d24d97e6a4f20c
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550469B2

Notizen zur Reaktion

Wird geladen…