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

Participants

Reaction Steps

Methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate (prepared according to Example 42; 70 mg, 0.17 mmol), KOtBu (0.59 mL, 0.59 mmol) and 3-(chloromethyl)pyridine hydrochloride (27.6 mg, 0.17 mmol were reacted according to the method of Example 43 to afford 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(pyridin-3-ylmethylthio)pyridin-2-amine dihydrochloride (44.2 mg, 53.2% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 8.68 (dd, 1H), 8.65 (d, 1H), 8.11 (m, 1H), 7.80-7.75 (m, 2H), 7.60-7.55 (m, 3H), 7.45-7.34 (m, 3H), 6.75 (s, 1H), 5.30 (s, 2H), 4.34 (s, 2H), 2.28 (d, 3H); Mass spectrum (apci) m/z=238.0 (100), 330.0 (70), 421.0 (60).

Provenance & Evidence