Sodium Hydroxide → HCID 10450477, compound

Participants

Reaction Steps

A solution of 4′-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Example 53) (30 mg) in acetic acid/water (1:1 v/v, 3 ml) was cooled to 0° C. Sodium nitrite (68 mg) was added and the solution stirred 24 hours at room temperature. Concentrated sodium hydroxide solution was added to the reaction and the mixture extracted with ether (3×20 ml). The combined organic phases were treated with potassium hydroxide in methanol (5%, 3 ml) for 2 hours, washed with water, dried (sodium sulphate) and reduced to dryness under vacuum. The residue was dissolved in 5% potassium hydroxide in methanol and stirred at room temperature for 90 minutes. The methanol was removed in vacuo, the residue partitioned between ethyl acetate/chloroform (1:1)/water and the organic phase dried and reduced to dryness under vacuum. This material was purified by HPLC, to give, after evaporation of the solvent, N-cyclopropyl-4′-[5-(hydroxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1′-biphenyl-3-carboxamide.

Provenance & Evidence