Hydrochloric Acid → 5-(2-chlorobenzylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride

Participants

Reaction Steps

A 1 dram vial was charged with methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate (prepared according to Example 42; 70 mg, 0.17 mmol). THF (1 mL) and KOtBu (0.59 mL, 0.59 mmol) were added and the reaction mixture was stirred at room temperature for 5 minutes. 1-(Bromomethyl)-2-chlorobenzene (0.024 mL, 0.19 mmol) was added and the reaction mixture was stirred at room temperature for 30 minutes. Saturated aqueous NH4Cl (1 mL) was added and the reaction mixture was stirred for 10 minutes. The phases were separated and the aqueous phases were washed with EtOAc. The combined organic layers were concentrated and purified on silica gel to afford 5-(2-chlorobenzylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (48.2 mg, 58.3% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 7.80 (d, 1H), 7.60-7.55 (m, 3H), 7.46-7.34 (m, 4H), 7.27 (td, 1H), 7.18 (td, 1H), 7.10 (dd, 1H), 6.81 (q, 1H), 5.31 (s, 2H), 4.22 (s, 2H), 2.30 (d, 3H); Mass spectrum (apci) m/z=238.0 (100), 454.0 (90), 362.9 (80).

Provenance & Evidence