Lawesson's reagent → {4-[5-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-[1,3,4]thiadiazol-2-yl]-6-methyl-pyridin-2-yl}-diethyl-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzyloxy-3-ethyl-5-methyl-benzoic acid N′-(2-diethylamino-6-methyl-pyridine-4-carbonyl)-hydrazide (1.29 g, 2.72 mmol, intermediate from Example 81 step a)) in THF (15 mL), Lawesson reagent (1.21 g, 2.99 mmol) is added. The mixture is stirred at 110° C. for 15 min under microwave irradiation (300 W, external cooling). The mixture is cooled to rt, diluted with EA (100 mL) and washed with sat. aq. Na2CO3-solution (3×50 mL) followed by brine (1×50 mL). The org. extract is dried over MgSO4, filtered, concentrated and dried to give crude {4-[5-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-[1,3,4]thiadiazol-2-yl]-6-methyl-pyridin-2-yl}-diethyl-amine (2.43 g) as a yellow oil; LC-MS: tR=1.01 min, [M+1]+=473.20.

Provenance & Evidence