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Dichloromethane → 5-(1-methylcyclopropyl)-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridine

HRID 546437
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 546437
Cl.[CH3:2][C:3]1([NH2:6])[CH2:5][CH2:4]1.ClCCl.CS(O[CH2:15][CH2:16][C:17]1[N:18]=[CH:19][S:20][C:21]=1[CH2:22]OS(C)(=O)=O)(=O)=O>O>[CH3:2][C:3]1([N:6]2[CH2:15][CH2:16][C:17]3[N:18]=[CH:19][S:20][C:21]=3[CH2:22]2)[CH2:5][CH2:4]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6344Dichloromethane2×HCID 12953687(1-Methylcyclopropyl)amine hydrochloride2×HCID 178424394-(2-Methane-sulfonyloxyethyl)-5-methanesulfonyloxymethylthiazole

Produkt 1

HCID 178424835-(1-methylcyclopropyl)-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridineAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

1-Methylcyclopropylamine hydrochloride (J. Org. Chem., 1989, Vol. 54, p. 1815) (1.89 g) was added to dichloromethane (20 ml) containing 4-(2-methane-sulfonyloxyethyl)-5-methanesulfonyloxymethylthiazole (4.46 g) under ice cooling, and the mixture was stirred overnight at room temperature. 1-Methylcyclopropylamine hydrochloride (1.89 g) was additionally added, and the mixture was stirred for 20 hours at room temperature and 5 hours under refluxing. Dichloromethane and water were added to the reaction mixture to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:49) to obtain the title compound (944 mg) as a pale yellow oil.

Aufarbeitung

  1. stirringthe mixture was stirred for 20 hours at room temperature and 5 hours
  2. temperatureunder refluxing
  3. customto separate an organic layer
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:49)

Quellen und Nachweise

ORD-Eintrag
ord-e5b9c0d083f44fa0919ec016e4371bbe
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935824B2

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