Methylamine → methyl-6-(4-(3-(methylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

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A mixture of 3-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate (1.5 g) and methylamine in THF (2M, 8.25 ml) in NMP (12 ml) was heated at 100° C. under microwave conditions for 30 minutes. The mixture was then columned on silica gel using DCM-DCM-MeOH (19:1) then MeOH-2M ammonia in MeOH as eluant to give the expected product (757 mg). 1H NMR (CD3OD) δ: 8.43 (s, 1H), 8.31-8.40 (m, 3H), 7.31 (d, 1H), 4.26 (t, 2H), 4.02 (s, 3H), 2.80 (t, 2H), 2.41 (s, 3H), 2.06 (quin, 2H). MS m/z 390 (M+H).

Provenance & Evidence