Tetrahydrofuran → N-cyclopropyl-N'-{2-[(3-fluoro-4-methylphenyl)amino]pyridin-3-yl}ethanediamide

HRID 2272692Notizen

Reaktionsgleichung

CC(C)([O-])C.[K+].[F:7][C:8]1[CH:9]=[C:10]([NH:15][C:16]2[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:11]=[CH:12][C:13]=1[CH3:14].C([O:25][C:26](=O)[C:27]([NH:29][CH:30]1[CH2:32][CH2:31]1)=[O:28])C.O1CCCC1>CN1CCCC1=O.[Cl-].[NH4+].C(OCC)(=O)C>[CH:30]1([NH:29][C:27](=[O:28])[C:26]([NH:22][C:21]2[C:16]([NH:15][C:10]3[CH:11]=[CH:12][C:13]([CH3:14])=[C:8]([F:7])[CH:9]=3)=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:25])[CH2:32][CH2:31]1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

Potassium tert-butoxide (4.54 g, 40.5 mmol) was added to a solution of N2-(3-fluoro-4-methylphenyl)pyridine-2,3-diamine (C2) (from the previous step, 5.87 g, 24.4 mmol) and ethyl(cyclopropylamino)(oxo)acetate (P1) (6.36 g, 40.5 mmol) in 1-methylpyrrolidin-2-one (27 mL). The reaction mixture was heated at 120° C. for 10 minutes, cooled to room temperature and diluted with aqueous ammonium chloride solution. Tetrahydrofuran was added to assist solubilization, followed by ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide the crude product (13.0 g). A portion of this material was used directly in the following step. LCMS m/z 329.0 [M+H]+.

Aufarbeitung

temperaturecooled to room temperature
washThe organic layer was washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-65777bdbd1f54d8cbe1175bc428b2683
Quelldatensatz: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09120788B2

Notizen zur Reaktion

Wird geladen…