Lithium hydroxide, monohydrate → HCID 178525548, compound

Participants

Reaction Conditions

Reaction Steps

Lithium hydroxide monohydrate (60 mg) in water (2 mL) was added to a stirred suspension of methyl {trans-4-[4-({[5-(pyridin-2-ylamino)-1,3,4-oxadiazol-2-yl]carbonyl}amino)phenyl]cyclohexyl}acetate (Example 105, 309 mg) in THF (7 mL). After 16 hours the solution was heated to 40° C. and stirred for a further 5 hours then allowed to cool to ambient temperature. The THF was removed in vacuo and the residue was acidified with 2M HCl. The precipitate was filtered off, washed with ether, warm DCM and warm ether then dried overnight. The resultant solid was purified by HPLC using a gradient of 5-25% MeCN in water with 1% ammonia as the eluent to give the title compound (119 mg) as a solid; 1H NMR δ 10.80 (1H, bs), 10.91 (1H, s), 8.31 (1H, d), 7.86 (2H, m), 7.69 (2H, d), 7.23 (2H, d), 7.05 (1H, m), 2.45 (1H+DMSO, m), 2.14 (2H, d), 1.82 (5H, m), 1.47 (2H, m), 1.13 (2H, m); MS m/e MH+ 422.

Provenance & Evidence