Acetyl chloride → (4-Chloro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)pyridin-3-yl)methyl acetate

HRID 592979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592979
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:20][CH2:19][C:18]3[N:17]4[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]4)=[CH:11][C:10]=3[C:9]2=[O:21])[C:3]=1[CH2:22][OH:23].C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl>[C:31]([O:23][CH2:22][C:3]1[C:4]([N:8]2[CH2:20][CH2:19][C:18]3[N:17]4[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]4)=[CH:11][C:10]=3[C:9]2=[O:21])=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:33])[CH3:32]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 866844622-(4-Chloro-3-(hydroxymethyl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1(2H)-one

Produkt 1

HCID 86684463(4-Chloro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)pyridin-3-yl)methyl acetateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

To a mixture of 244a (900 mg, 2.7 mmol) and triethylamine (810 mg, 8.1 mmol) in dichloromethane (30 mL) was added acetyl chloride (630 mg, 8.1 mmol) dropwise. The reaction mixture was stirred at 30° C. for 1 h. It was then concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with dichloromethane to afford 244b as white solid (900 mg, 90%). MS-ESI: [M+H]+ 374.2

Aufarbeitung

  1. concentrationIt was then concentrated under reduced pressure
  2. customthe residue was purified by silica-gel column chromatography
  3. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b9998a93f68b4c3a92b0f14173e74c5a
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238655B2

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