Hydrogen Bromide → 5-(azetidin-3-ylamino)-2'-(methylamino)-[3,4'-bipyridin]-6(1H)-one di-hydrobromide

Participants

Reaction Steps

A solution of tert-butyl 3-((6-methoxy-2′-(methylamino)-[3,4′-bipyridin]-5-yl)amino)azetidine-1-carboxylate (890 mg, 2.31 mmol) in 40% HBr (9 mL) was stirred at 50° C. for 14 h. After the mixture was cooled to RT, 9 mL of methanol was added, the residue filtered, washed with ethyl acetate (5 mL), and dried in vacuo to afford 5-(azetidin-3-ylamino)-2′-(methylamino)-[3,4′-bipyridin]-6(1H)-one di-hydrobromide (947 mg, 89%) as yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 12.97 (s, 1H), 12.18 (d, J=5.9 Hz, 1H), 8.87 (s, 1H), 8.68 (s, 1H), 8.50 (s, 1H), 7.89 (d, J=6.8 Hz, 1H), 7.52 (dd, J=5.8, 2.6 Hz, 1H), 7.23 (s, 1H), 7.20 (dd, J=7.0, 1.8 Hz, 1H), 6.60 (s, 1H), 6.50 (d, J=2.5 Hz, 1H), 4.48 (d, J=8.9 Hz, 1H), 4.34 (m, 2H), 4.09-3.97 (m, 2H), 2.99 (d, J=4.8 Hz, 3H); MS (ES) m/z 272 (M+H).

Provenance & Evidence