tert-butyl (5-methyl-1,3,4-thiadiazol-2-yl)methyl(2-methyl-6-(((1S,2S)-2-(5-methyl pyridin-2-yl)cyclopropyl)methoxy)-3-oxo-2,3-dihydropyridazin-4-yl)carbamate → 2-methyl-4-((5-methyl-1,3,4-thiadiazol-2-yl)methylamino)-6-(((1S,2S)-2-(5-methyl pyridin-2-yl)cyclopropyl)methoxy)pyridazin-3(2H)-one

Participants

Reaction Steps

A solution of tert-butyl (5-methyl-1,3,4-thiadiazol-2-yl)methyl(2-methyl-6-(((1S,2S)-2-(5-methyl pyridin-2-yl)cyclopropyl)methoxy)-3-oxo-2,3-dihydropyridazin-4-yl)carbamate (7) (95 mg, 0.19 mmol) in TFA (1 mL) was stirred at room temperature for 1 h. The reaction mixture was concentrated and 10 mL sat. aq. NaHCO3 was added, extracted with EA (3×10 mL). The organic phase was dried with anhydrous Na2SO4, filtered and concentrated. The residue was purified by Prep-TLC using PE/EtOAc=1/2 to give title compound as a oil. 1H NMR (400 MHz, DMSO) δ 8.23 (s, 1H), 7.55 (t, 1H), 7.45 (d, 1H), 7.18 (d, 1H), 5.86 (s, 1H), 4.73-4.71 (m, 2H), 4.09-4.04 (m, 1H), 3.97-3.97 (m, 1H), 3.51 (s, 3H), 2.66 (s, 3H), 2.22 (s, 3H), 2.11-2.05 (m, 1H), 1.72-1.68 (m, 1H), 1.14-1.09 (m, 1H), 0.99-0.94 (m, 1H); LRMS m/z (M+H) 399.2 found, 399.15 required.

Provenance & Evidence