Ethylene Glycol → HCID 178434333, compound

Participants

Reaction Conditions

Reaction Steps

4-((2-(3-methyl-1H-indazol-6-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-ylmethyl)pyridin-2(1H)-one. To a solution/suspension of (2-methoxypyridin-4-yl)(2-(3-methyl-1H-indazol-6-ylamino)-[1,2,4]triazolo[1,5-c]pyridin-5-yl)methanone (400 mg, 0.847 mmol), in a 50 mL pressure vial, hydrazine hydrate (1.232 mL, 25.4 mmol), and potassium hydroxide (1188 mg, 21.17 mmol) were added followed by ethylene glycol (10 mL). The reaction mixture was heated to 190° C., and was left to stir overnight, then checked by LCMS. Once the reaction was complete, water was added to the crude mixture and the product was extracted with ethyl acetate three times. The organics were washed with brine and dried over sodium sulfate. The crude was purified on semi-preparative HPLC (20-100% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, 20 min). The fractions containing the product were loaded on a strata-X column to remove trifluoroacetic acid, then methanol was evaporated in vacuo. 4-((2-(3-methyl-1H-indazol-6-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)methyl)pyridin-2-ol (15 mg, 0.040 mmol, 4.77% yield) was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 12.38 (s, 1H), 11.70 (br s, 1H), 9.76 (s, 1H), 8.07 (d, J=1.17 Hz, 1H), 7.56-7.65 (m, 1H), 7.49-7.55 (m, 2H), 7.34 (d, J=6.64 Hz, 1H), 7.08 (td, J=1.56, 7.81 Hz, 2H), 6.53 (d, J=0.78 Hz, 1H), 6.19 (dd, J=1.56, 6.64 Hz, 1H), 4.31 (s, 2H), 2.43 (s, 3H); MS (ESI): m/z 371.7 [M+1]+.

Provenance & Evidence