Diisopropylethylamine → HCID 178458649, Verbindung

HRID 2189852

Reaktionsgleichung

[Cl:1][C:2]1[C:3]([NH:12][C:13]2[CH:17]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[NH:15][N:14]=2)=[N:4][C:5](Cl)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C@@H:29]([NH2:31])[CH3:30])=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:1][C:2]1[C:3]([NH:12][C:13]2[CH:17]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[NH:15][N:14]=2)=[N:4][C:5]([NH:31][C@H:29]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[CH3:30])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 145 °C

Versuchsvorschrift

A mixture of 3,6-dichloro-N-(5-isopropoxy-1H-pyrazol-3-yl)-5-nitropyridin-2-amine (Method 27, 0.25 g, 0.75 mmol), (s)-1-(4-fluoro-phenyl)-ethylamine (0.13 g, 0.90 mmol) and DIEA (0.16 ml, 0.94 mmol) in n-BuOH (3 ml) was heated in a sealed tube at 145° C. for 2 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane-EtOAc=1:1) to give the title compound as a yellow solid (0.32 g, 98%). 1H NMR (400 MHz) δ 12.22 & 11.40 (s, 1H), 9.74 & 9.37 (s, 1H), 8.93 (d, J=7.6 Hz, 1H), 8.33 & 8.27 (s, 1H), 7.34 & 7.27 (m, 2H), 7.12 & 7.05 (m, 2H), 5.75 & 5.62 (s, 1H), 5.35 & 5.25 (m, 1H), 4.66 & 4.03 (m, 1H), 1.55 (d, J=6.4 Hz, 3H), 1.29 (d, J=6.0 Hz, 6H). MS: Calcd.: 434. Found: [M+H]+ 435.

Aufarbeitung

customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography (hexane-EtOAc=1:1)

Quellen und Nachweise

ORD-Eintrag: ord-86a6878e1b76458fae607c840a828ddd
Quelldatensatz: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08324252B2

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