4,6-Dichloropyrimidine → N-{3-[1-(6-chloro-pyrimidin-4-yl)-1H-imidazol-2-ylamino]-4-methyl-phenyl}-3-trifluoromethyl-benzamide

HRID 19495

Reaktionsgleichung

[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]1[CH:8]=[C:9]([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[CH:10]=[CH:11][C:12]=1[CH3:13].[Cl:27][C:28]1[CH:33]=[C:32](Cl)[N:31]=[CH:30][N:29]=1.C(N(CC)C(C)C)(C)C>CC(O)CC>[Cl:27][C:28]1[N:29]=[CH:30][N:31]=[C:32]([N:1]2[CH:5]=[CH:4][N:3]=[C:2]2[NH:6][C:7]2[CH:8]=[C:9]([NH:14][C:15](=[O:26])[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=3)[CH:10]=[CH:11][C:12]=2[CH3:13])[CH:33]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of N-[3-(1H-Imidazol-2-ylamino)-4-methyl-phenyl]-3-trifluoromethyl-benzamide (330 mg, 0.92 mmol), 4,6-dichloropyrimidine (409 mg, 2.75 mmol), N,N-diisopropylethyl amine (500 μL, 2.87 mmol) in 2-butanol (20 mL) is heated at 110° C. After 16 hours, the reaction mixture is concentrated. The solid is washed with saturated sodium carbonate, water, ethyl acetate, and dried to give the title compound. 1H NMR 600 MHz (DMSO-d6) δ 10.71 (s, 1H), 10.50 (s, 1H), 9.09 (s, 1H), 8.80 (s, 1H), 8.33 (s, 1H), 8.29 (d, J=7.8 Hz, 1H), 8.17 (s, 1H), 7.96 (d, J=8.4 Hz, 1H), 7.84 (s, 1H), 7.77 (t, J=8.4 Hz, 1H), 7.42 (d, J=7.2 Hz, 1H), 7.21 (d, J=8.4 Hz, 1H), 6.95 (s, 1H), 2.38 (s, 3H); MS m/z 473.3 (M+1).

Aufarbeitung

concentrationthe reaction mixture is concentrated
washThe solid is washed with saturated sodium carbonate, water, ethyl acetate
customdried

Quellen und Nachweise

ORD-Eintrag: ord-ca0b4baae053415c9b2d4bcefe18a839
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745437B2

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