Sodium Hydroxide → HCID 58456138, compound

Participants

Reaction Steps

A microwave vessel was charged with a solution of the compound of Step 3 (10 mg, 0.019 mmol) in MeOH, and sodium hydroxide (1.0 N in H2O, 56 μl, 0.056 mmol, 3 equiv) was added. The resultant cloudy orange suspension was irradiated in the microwave at 110° C. for 15 min. The reaction was not complete. Additional sodium hydroxide (1.0 N in H2O, 190 uL, 0.19 mmol, 10 eq) was added and the faintly yellow solution was irradiated at 150° C. for 30 min. The reaction mixture was concentrated in vacuo, then partitioned between diethyl ether (75 ml) and water (85 ml). The aqueous layer was acidified with 1N aqueous HCl to pH ˜3-4, then washed with EtOAc (2×35 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated, affording the title compound (3.6 mg, 35%) as an orange oil. MS ESI: [M+H]+ m/z 522.2 1H NMR (500 MHz, DMSO-d6) δ 10.5 (s, 1H), 8.85 (d, J=4.9 Hz, 1H), 8.24 (bs, 1H), 8.14 (s, 1H), 7.93 (s, 1H), 7.65 (s, 1H), 7.46 (s, 1H), 7.33 (d, J=4.9 Hz, 1H), 5.94 (bs, 1H), 4.03-3.99 (m, 3H), 3.14 (m, 2H), 2.19-2.16 (m, 2H), 1.86-1.83 (m, 2H), 1.66-1.60 (m, 2H), 1.17-1.11 (m, 6H). rhSYK activity=+++

Provenance & Evidence