(E)-pent-2-enoyl chloride → HCID 56949206, Verbindung

HRID 333971

Reaktionsgleichung

Reaktionsgleichung von HRID 333971
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[N:6]2[N:15]=[CH:16][CH:17]=[C:5]2[N:4]=1.[C:18](Cl)(=[O:23])/[CH:19]=[CH:20]/[CH2:21][CH3:22]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:10][CH2:11][N:12]([C:18](=[O:23])/[CH:19]=[CH:20]/[CH2:21][CH3:22])[CH2:13][CH2:14]2)[N:6]2[N:15]=[CH:16][CH:17]=[C:5]2[N:4]=1

Komponenten

4

Edukt 2

HCID 5706546(E)-pent-2-enoyl chlorideHCID 66835729HCID 66835729, Verbindung

Produkt 1

HCID 56949206HCID 56949206, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

5-Methoxy-7-piperazin-1-yl-pyrazolo[1,5-a]pyrimidine (23.3 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (1 ml), TEA (17.4 μl, 1.25 mmol) followed by (E)-pent-2-enoyl chloride (14.8 mg, 0.125 mmol) were added, the mixture was shaken for 10 minutes, diluted with dichloromethane, washed with 10% sodium bicarbonate solution, water and the organic phase was evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 16.1 mg of a solid (0.05 mmol, 51%).

Aufarbeitung

  1. additionwere added
  2. washwashed with 10% sodium bicarbonate solution, water
  3. customthe organic phase was evaporated to dryness under reduced pressure
  4. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-e503c9f02bcb4dc2ac00b64268061954
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883791B2

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