Methanesulfonic Acid → HCID 57524120, compound

Participants

Reaction Steps

In a 100-mL, 3N round-bottomed flask equipped with Thermometer pocket fitted with nitrogen inlet, condenser and a rubber septum, (Z)-3-(3-(2-chloro-6-methoxypyridin-4-yl)-1H-1,2,4-triazol-1-yl)acrylohydrazide (0.7 g, 1.0 eq.), trimethyl orthoformate (0.3 mL, 1.1 eq.) and methane sulfonic acid (0.07 mL, 0.5 eq) was dissolved in THF (70 mL) resulting reaction mixture was stir at reflux temperature. The progress of the reaction was followed by TLC analysis on silica gel with 80% EtOAc-hexane as mobile phase which shows that starting material was consumed after 3 h. Reaction was quenched by water, solid material was observed that was filter on Buchner funnel to give crude material (0.490 g). The crude material was subjected to combiflash purification using ethyl acetate:hexane as mobile phase; Yield: 0.03 g (4.14%); (Z)-2-(2-(3-(2-chloro-6-methoxypyridine-4-yl)-1H-1,2,4-triazol-1-yl)vinyl)-1,3,4-oxadiazole: 1H NMR: (400 MHz, DMSO) δ=9.45 (s, 1H), 9.36 (s, 1H), 7.737-7.762 (d, J=10 Hz, 1H), 7.48 (s, 1H), 7.24 (s, 1H), 6.719-6.745 (d, J=10.4 Hz, 1H), 3.92 (s, 3H). LC-MS: Calculated for C12H9ClN6O2 (M+H)+ 304.69 Found: 304.81 Retention time: 3.354 min (100%).

Provenance & Evidence