Diisopropylethylamine → 3-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-nitrobenzonitrile

HRID 1092248

Reaktionsgleichung

F[C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].CCN(C(C)C)C(C)C.[CH:23]1([C:26]2[NH:30][N:29]=[C:28]([NH2:31])[CH:27]=2)[CH2:25][CH2:24]1>C1COCC1>[CH:23]1([C:26]2[NH:30][N:29]=[C:28]([NH:31][C:2]3[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=3)[C:5]#[N:6])[CH:27]=2)[CH2:25][CH2:24]1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a solution of 3,5-difluoro-2-nitrobenzonitrile (Method 99, 5.8 g, 31.5 mmol) and DIEA (5.5 ml, 31.5 mmol) in THF (50 ml) was added drop wise a solution of 5-cyclopropyl-1H-pyrazol-3-amine (4.66 g, 37.8 mmol) in THF (5 ml) at 0° C. After addition, the reaction mixture was stirred at 25° C. for 20 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (DCM-EtOAc=10:1) to give the title compound as a yellow solid (5.5 g, 61%). 1H NMR (400 MHz) 12.43 (s, 1H), 9.70 (s, 1H), 8.22 (dd, J=11.2 and 2.0 Hz, 1H), 7.51 (d, J=5.2 Hz, 1H), 5.92 (s, 1H), 1.90 (m, 1H), 0.95 (m, 2H), 0.71 (m, 2H). MS: Calcd.: 287; Found: [M+H]+ 288.

Aufarbeitung

additionAfter addition
customThe solvent was removed under reduced pressure
customthe resulted residue was purified by column chromatography (DCM-EtOAc=10:1)

Quellen und Nachweise

ORD-Eintrag: ord-7955c17079794c4cbc36c30df021fddf
Quelldatensatz: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08129403B2

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