Sodium Nitrite → 6-(4-(3-hydroxypropoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

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Reaction Steps

A solution of sodium nitrite (13.07 g) in water (40 ml) was added to 3-amino-6-(4-(3-hydroxypropoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)picolinonitrile (49.6 g) in 2M hydrochloric acid (203 ml) and NMP (180 ml). The mixture was stirred at room temperature for 2 hours then diluted with ethyl acetate (50 mml), and the mixture washed with water (300 ml+100 ml×4), the organic layer was dried over magnesium sulphate, solvent removed under reduced pressure. The residue was then columned on silica gel using DCM then DCM-MeOH (199:1) as eluant to give expected product (10.34 g). 1H NMR (CD3OD) δ: 8.55 (s, 1H), 8.39-8.45 (m, 2H), 7.35 (d, 1H), 4.45 (s, 3H), 4.30 (t, 2H), 3.80 (t, 2H), 2.06 (quin, 2H). MS m/z 378 (M+H).

Provenance & Evidence