Potassium Hydroxide → (4-Cyclobutyl-[1,4]diazepan-1-yl)-[6-(tetrahydro-pyran-4-yloxy)-pyridin-3-yl]-methanone

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Reaktionsgleichung

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH:17]3[CH2:20][CH2:19][CH2:18]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[O:21]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]1.C1OCCOCCOCCOCCOCCOC1.[OH-].[K+]>C1(C)C=CC=CC=1.O>[CH:17]1([N:13]2[CH2:14][CH2:15][CH2:16][N:10]([C:8]([C:5]3[CH:6]=[N:7][C:2]([O:27][CH:24]4[CH2:25][CH2:26][O:21][CH2:22][CH2:23]4)=[CH:3][CH:4]=3)=[O:9])[CH2:11][CH2:12]2)[CH2:20][CH2:19][CH2:18]1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

To a solution of (6-chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone (32.7 g, 111.3 mmol) in toluene (470 mL) was added tetrahydro-pyran-4-ol (13.6 g, 133.6 mmol), 18-crown-6 (1.47 g, 5.565 mmol), and then KOH (pulverized solid, 20.6 g, 367.3 mmol). The resulting heterogeneous mixture was warmed to 110° C. and stirred for 3 h. After cooling to room temperature, water (470 mL) was added and the resulting layers were thoroughly mixed and then separated. The organic extract was dried over magnesium sulfate, filtered, and concentrated to yield the title compound as a yellow oil.

Aufarbeitung

temperatureAfter cooling to room temperature
additionthe resulting layers were thoroughly mixed
customseparated
extractionThe organic extract
dry with materialwas dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-b63d9d3acc1f403fa4ac76e4def26d5c
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08748596B2

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