Diisopropylethylamine → HCID 58557985, Verbindung

HRID 1969512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969512
Cl.[F:2][C:3]1([F:7])[CH2:6][NH:5][CH2:4]1.CCN(C(C)C)C(C)C.FC(F)(F)S([O-])(=O)=O.[N:25]1([S:30](N2C=C[N+](C)=C2)(=[O:32])=[O:31])[CH:29]=[CH:28][N:27]=[CH:26]1>CC#N>[F:2][C:3]1([F:7])[CH2:6][N:5]([S:30]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)(=[O:32])=[O:31])[CH2:4]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 117281493-(Imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate

Produkt 1

HCID 58557985HCID 58557985, VerbindungAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3,3-difluoroazetidine hydrochloride (1.00 g, 7.72 mmol) and DIEA (1.5 mL, 8.6 mmol) in MeCN (5 mL) was stirred for about 5 min and then was added to a solution of 1-(1H-imidazol-1-ylsulfonyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate (4.20 g, 11.6 mmol) in MeCN (10 mL) at about 0° C. The reaction mixture was stirred at about 0° C. for about 1 h, and then warmed to ambient temperature and stirred for about 16 h. The reaction mixture was then concd under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with a gradient of 5-100% EtOAc in DCM to give 1-(3,3-difluoroazetidin-1-ylsulfonyl)-1H-imidazole (0.95 g, 55%) as a yellow solid: LC/MS (Table 1, Method c) Rt=1.16 min; MS m/z 224 (M+H)+.

Aufarbeitung

  1. temperaturewarmed to ambient temperature
  2. stirringstirred for about 16 h
  3. customThe crude material was purified by flash chromatography on silica gel eluting with a gradient of 5-100% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag
ord-277da7afc80d4eaeabdcfba1e669ddc3
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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