Sodium Hydroxide → HCID 178525549, compound

Participants

Reaction Steps

To a solution of methyl (trans-4-{5-[({5-[(2,4,5-trifluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridin-2-yl}cyclohexyl)acetate (Example 406, 355 mg, 0.725 mmol) in THF (5 mL) and MeOH (25 mL) was added a 2M solution of NaOH (1.8 mL). The resulting yellow solution was allowed to stir at ambient temperature for 16 hr then a further 1.8 mL of 2M NaOH was added and stirring was continued at ambient temperature for 16 hr. The volatile organics were removed by evaporation and residue adjusted to pH ˜1 with 2M HCl and the suspension was filtered and dried to leave 410 mg of a solid. This was suspended in acetic acid (4 mL) and heated to 120° C., giving an incomplete solution. This was allowed to cool, filtered and washed with water then dried overnight, to give the title compound (167 mg, 48%) as a solid; 1H NMR (CDCl3) δ 1.10-1.19 (m, 2H), 1.56-1.65 (m, 2H), 1.72-1.79 (m, 1H), 1.85-1.94 (m, 4H), 2.17 (d, 2H), 2.79-2.85 (m, 1H), 7.67-7.76 (m, 2H), 8:12-8.19 (m, 1H), 8.44 (d, 1H), 9.01 (s, 1H), 11.14 (s, 1H), 11.58 (s, 1H), CO2H not seen; MS m/e MH+ 476.

Provenance & Evidence