Morpholine → 4-Morpholin-4-yl-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine

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Reaktionsgleichung

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])[N:5]=[C:4]([NH2:18])[C:3]=1[N+:19]([O-:21])=[O:20].C([O-])([O-])=O.[K+].[K+].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>CN(C=O)C.O>[N:28]1([C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:14]([F:17])([F:16])[F:15])[N:5]=[C:4]([NH2:18])[C:3]=2[N+:19]([O-:21])=[O:20])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 4-chloro-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine (900 mg, 2.83 mmol, prepared as described in the Example 1) in DMF (5 mL), K2CO3 (1.90 g, 14.0 mmol) was added followed by addition of morpholine (0.240 mL, 2.80 mmol). The resulting mixture was stirred at 80° C. overnight. The resulting mixture was diluted with water (20 mL) and extracted with EtOAc (3×10 mL). The organic layers were combined, dried (MgSO4) and concentrated. The resulting residue was purified on silica 0:100-50:50 EtOAc/hexanes to yield 4-morpholin-4-yl-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine. Mass Spectrum (LCMS, ESI pos.) Calculated For Mass Spectrum (LCMS, ESI pos.) Calculated For C16H15F3N4O3: 369.1 (M+H). Measured: 369.1.

Aufarbeitung

extractionextracted with EtOAc (3×10 mL)
dry with materialdried (MgSO4)
concentrationconcentrated
customThe resulting residue was purified on silica 0:100-50:50 EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag: ord-280dd575076a4f3bba61eb93b65573cd
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09409915B2

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