Phosphorus oxychloride → 5-Chloro-7-(2,4-difluorophenyl)-2-[1-(propan-2-yl)piperidin-4-yl][1,2,4]triazolo[1,5-c]pyrimidine hydrochloride

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Reaktionsgleichung

P(Cl)(Cl)([Cl:3])=O.[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]1[NH:19][C:18](=O)[N:17]2[N:21]=[C:22]([CH:24]3[CH2:29][CH2:28][N:27]([CH:30]([CH3:32])[CH3:31])[CH2:26][CH2:25]3)[N:23]=[C:16]2[CH:15]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[ClH:3].[Cl:3][C:18]1[N:17]2[N:21]=[C:22]([CH:24]3[CH2:29][CH2:28][N:27]([CH:30]([CH3:32])[CH3:31])[CH2:26][CH2:25]3)[N:23]=[C:16]2[CH:15]=[C:14]([C:8]2[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:7]=2[F:6])[N:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

4.5 ml of phosphoryl chloride were added to 670 mg (1.72 mmol) of 7-(2,4-difluorophenyl)-2-[1-(propan-2-yl)piperidin-4-yl][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 51A), 785 mg (3.45 mmol) of benzyltriethylammonium chloride were added and the reaction mixture was stirred at 120° C. for 7 h. The reaction mixture was concentrated and carefully, with vigorous stirring, added to ice. Three times, the aqueous phase was extracted with dichloromethane. The combined organic phases were freed from the solvent and used without further purification. This gave 590 mg (80% of theory) of the product.

Aufarbeitung

additionwere added
concentrationThe reaction mixture was concentrated
additioncarefully, with vigorous stirring, added to ice
extractionThree times, the aqueous phase was extracted with dichloromethane
customused without further purification

Quellen und Nachweise

ORD-Eintrag: ord-66d6830e2db04b5fb7eabc29df13352f
Quelldatensatz: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08436003B2

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