Hydrochloric Acid → 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(pyridin-4-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 4-(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-4-ylmethylthio)pyridin-2-amine dihydrochloride (47.9 mg, 57.6% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 8.72 (m, 2H), 7.77 (d, 1H), 7.71 (m, 2H), 7.58 (m, 3H), 7.45-7.34 (m, 3H), 6.73 (s, 1H), 5.30 (s, 2H), 4.42 (s, 2H), 2.27 (d, 3H); Mass spectrum (apci) m/z=421.0 (100), 330.0 (45), 238.0 (40).

Provenance & Evidence