Isonicotinic Acid → HCID 68554551, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of isonicotinic acid 13 (900 mg, 4.73 mmol), 4-benzyloxy-3-ethyl-5-methyl-benzoic acid hydrazide (2848 mg, 5.00 mmol) and DIPEA (1.73 g, 13.4 mmol) in DCM (50 mL), PyBOP (3257 mg, 6.26 mmol) is added at 0° C. The mixture is stirred at 0° C. for 30 min before it is diluted with EA, washed with sat. aq. NaHCO3-solution. The org. extract is dried over Na2SO4, filtered and concentrated to give the crude di-acylhydrazide; LC-MS: tR=0.74 min, [M+1]+=446.09. This material and Lawesson reagent (1.86 g, 4.59 mmol) are dissolved in THF (15 mL) and the mixture is heated in the microwave at 110° C. for 5 min. The mixture is diluted with EA, washed with sat. aq. Na2CO3 solution, dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 4-[5-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-[1,3,4]thiadiazol-2-yl]-2-isopropyl-6-methyl-pyridine (837 mg) as a yellow oil; LC-MS: tR=1.00 min, [M+1]+=444.23.

Provenance & Evidence