Sodium Hydroxide → HCID 72188385, compound

Participants

Reaction Steps

To a reaction vial containing methyl 2-(4-(4-(5-(5-tert-butyl-1,3,4-oxadiazol-2-ylamino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (55 mg, 0.12 mmol) was added THF (1.5 ml) and a solution of 1N NaOH (0.35 ml, 0.35 mmol). The mixture was stirred vigorously at room temperature for overnight. The resulting mixture was concentrated to dryness and the residue was taken up in water. The mixture was acidified with 1N HCl to a pH of between 3 and 4 affording a thick residue. The residue was concentrated to dryness and taken up in MeOH to form fine slurry. The slurry was filtered and washed with small amount of MeOH and water to afford the title compound as white solid after drying (36 mg, 67% yield). HR/MS (M+H)+ found 463.2354. calc. 463.2345. RT: 5.76 (Condition Z). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.09 (br. s, 1H) 10.78 (br. s, 1H) 8.76 (d, J=2.78 Hz, 1H) 8.04-8.13 (m, 1H) 7.90-8.01 (m, 3H) 7.41 (d, J=8.59 Hz, 2H) 3.90 (s, 2H) 2.29 (s, 2H) 1.82-2.08 (m, 8H) 1.36 (s, 9H)

Provenance & Evidence