Triethylamine → HCID 67951154, Verbindung

HRID 923653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923653
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[S:9][NH:10][C:11](=[O:12])[C:3]=12.Cl[CH2:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16].CCN(CC)CC>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[S:9][N:10]=[C:11]([O:12][CH2:14][C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])[C:3]=12

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 74040Morpholine, 4-(chloroacetyl)-HCID 173760Isothiazolo(5,4-b)pyridin-3(2H)-one, 4,6-dimethyl-

Produkt 1

HCID 67951154HCID 67951154, VerbindungAusbeute 9,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Pyridinothiazolone 4 (200 mg, 1.22 mmol), was treated with 2-chloro-1-morpholinoethanone (225 mg, 1.25 mmol) and Et3N (370 mg, 3.66 mmol) in anhydrous CH2Cl2 (25 mL) at reflux (40° C.) for 24 h, and then washed with 1 M HCl(aq). The organic phase was dried over MgSO4, filtered, concentrated, and purified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:1) to give the title compound (35 mg, 9% yield) in addition to the main N-alkylation product 19 (55%).

Aufarbeitung

  1. washwashed with 1 M HCl(aq)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-cc79e810608d4c4c9b976b1139d63eac
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278982B2

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