Formaldehyde → HCID 21074209, compound

Participants

Reaction Steps

Formaldehyde (37% wt. in water) (0.021 ml, 0.75 mM) was added to a solution of 2-[3-amino-5-(4-methyl-thiazol-5-yl) ethoxy benzoyl]amino-5-pyridine carboxylic acid (0.10 g 0.25 mM) and 4A molecular sieves (0.25 g) in methanol (15 ml), under an inert atmosphere at room temperature. After 1 hr sodium cyanoborohydride (0.019 g, 0.3 mM) was added and the reaction mixture stirred for 40 hrs. The reaction mixture was filtered, concentrated in vacuo, 2M NaOH added to pH=11–12 then acidified with 2M HCl to precipitate a solid. The solid was filtered, washed with water, dried and purified on silica gel (5% to 12% MeOH/DCM) to give the title compound as a pale yellow solid (0.020 g, 19%); 1H NMR δ (d6-DMSO): 2.36 (s, 3H), 2.95 (m, 2H), 4.19 (dd, 2H), 6.39 (s, 1H), 6.92 (m, 2H), 6.99 (s, 1H), 8.27 (s, 2H), 8.83 (s, 1H), 8.88 (s, 1H), 11.02 (bs, 1H).

Provenance & Evidence