Ammonia → 3-(6-Fluorooxazolo[4,5-b]pyridin-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine

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Reaction Steps

A suspension of tert-butyl 4-[4-[6-amino-5-(6-fluorooxazolo[4,5-b]pyridin-2-yl)-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate (190 mg) and hydrogen chloride (4M solution in dioxane) (4.95 ml) in dichloromethane (2 ml) was stirred at room temperature for 2 hours. The resulting precipitate was collected by filtration, washed with diethyl ether and dried to afford a solid, which was taken up into 5% methanolic ammonia (7 N) in dichloromethane (20 ml) and stirred for 10 minutes. The suspension was filtered, concentrated and the resulting solid was stirred in acetonitrile (2 ml) for 2 hours at room temperature. It was collected by filtration and dried to a constant weight to afford 3-(6-fluorooxazolo[4,5-b]pyridin-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (110 mg). NMR Spectrum: (CDCl3) 1.88-2.03 (m, 2H), 2.18-2.27 (m, 2H), 2.76-2.84 (m, 2H), 3.23-3.33 (m, 2H), 4.23-4.33 (m, 1H), 6.86 (bs, 2H), 7.67 (dd, 1H), 7.70 (s, 1H), 7.78 (s, 1H), 8.36 (d, 1H), 8.44 (d, 1H), 8.48 (dd, 1H); Mass spectrum: M+H+ 380.

Provenance & Evidence