Hydrochloric Acid → HCID 46214654, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL flask under argon were combined N-[6-(2,6-diamino-4-pyrimidinyl)-1H-indazol-3-yl]acetamide (0.083 g, 0.29 mmol) and HCl (0.28 mL, 9.4 mmol, 12 M) in CH3OH (20 mL). The reaction mixture was stirred at 60° C. for 8 hours and then cooled to room temperature overnight. The mixture was concentrated and the resulting yellow solid was dissolved in water (3 mL). NaOH (1M) was added to the solution until the pH was 12. The precipitated solid was filtered, washed with water, and dried under vacuum at 40° C. The solid (18 mg) was dissolved in hot DMSO (0.5 mL) and sonicated. The resulting precipitate was filtered. Since HPLC showed the material to be only 90% pure, everything was combined (solids and filtrate) and purified on a Gilson RPHPLC (CH3CN/H2O w/0.1% NH4OH) to afford the title compound (7 mg, 10%) as a white solid. LC-MS (ES) m/z=242 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 5.37 (s, 2H), 5.93 (s, 2H), 6.25 (s, 1H), 6.31 (s, 2H), 7.40 (dd, J=8.3, 1.3 Hz, 1H), 7.69 (d, J=8.3 Hz, 1H), 7.82 (s, 1H), 11.51 (s, 1H).

Provenance & Evidence