1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-methyl-3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]butanenitrile

HRID 595284

Reaktionsgleichung

[CH3:1][C:2]([CH3:6])=[CH:3][C:4]#[N:5].C1CCN2C(=NCCC2)CC1.[CH3:18][C:19]1[CH:20]=[C:21]([NH:30][C:31]2[N:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][N:32]=2)[CH:22]=[C:23]([C:25]2[CH:26]=[N:27][NH:28][CH:29]=2)[CH:24]=1>C(#N)C>[CH3:1][C:2]([N:27]1[CH:26]=[C:25]([C:23]2[CH:22]=[C:21]([NH:30][C:31]3[N:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][N:32]=3)[CH:20]=[C:19]([CH3:18])[CH:24]=2)[CH:29]=[N:28]1)([CH3:6])[CH2:3][C:4]#[N:5]

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

3-Methylbut-2-enenitrile (179 mg, 1.57 mmol) and DBU (143 mg, 0.94 mmol) were added to a stirred solution of N-[3-methyl-5-(1H-pyrazol-4-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (250 mg, 0.73 mmol) in acetonitrile (3.9 mL). The mixture was heated to 75° C. overnight and concentrated under reduced pressure The residue was purified by column chromatography on silica gel to afford 3-methyl-3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]butanenitrile. MS ESI calcd. for C20H20F3N6 [M+H]+ 401. found 401. 1H NMR (500 MHz, DMSO-d6) δ 10.13 (s, 1H), 8.82 (d, J=4.9 Hz, 1H), 8.27 (s, 1H), 7.91 (s, 1H), 7.84 (s, 1H), 7.32 (s, 1H), 7.26 (d, J=4.9 Hz, 1H), 7.15 (s, 1H), 3.24 (s, 2H), 2.31 (s, 3H), 1.67 (s, 6H).

Aufarbeitung

concentrationconcentrated under reduced pressure The residue
customwas purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-6923a229a53443b1946ee39412a2b813
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09242984B2

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