p-Toluenesulfonic acid → HCID 86758134, compound

Participants

Reaction Steps

To a solution of 5-[1-(1,1-dimethyl-2-propynyl)-(2S)-azetidinylmethoxy]-2-fluoropyridine (58 mg, 0.23 mmol) from step 111a above in EtOH (3 mL) was added p-toluenesulfonic acid.monohydrate (44 mg, 0.23 mmol). The solution was stirred for 1 hour, then the volatiles were removed under vacuum. The solid was triturated with Et2O then dried under high vacuum to afford 93 mg (95%) of the the title compound as a white solid: mp 155-157° C.; 1H NMR (D2O) δ1.55 (s, 3H), 1.62 (s, 3H), 2.40 (s, 3H), 2.55 (m, 2H), 3.26 (s, 1H), 4.06 (m, 1H), 4.21 (m, 1H), 4.42 (d, J=4.0 Hz, 2H), 5.05 (m, 1H), 7.10 (dd, J=2.6, 8.8 Hz, 1H), 7.38 (d, J=8.1 Hz, 2H), 7.67 (m, 1H), 7.70 (d, J=8.5 Hz, 2H), 7.91 (m, 1H); MS (CI/NH3) m/z 249 (M+H+). Anal. Calcd for C14H17FN2O.C7H8O3S: C, 59.98; H, 5.99; N, 6.66. Found: C, 59.78; H, 5.91; N, 6.52.

Provenance & Evidence