Sodium Hydroxide → HCID 86641107, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 4-(2-(3-(1-acetylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-phenoxypyridin-3-ylthio)benzoate (0.15 g, 0.26 mmol) in EtOH was treated with NaOH (0.56 mL, 0.56 mmol). The solution was stirred at 60° C. for 1 hour. The solution was concentrated to give sodium (3-(1-acetylpiperidin-4-yl)-1,2,4-thiadiazol-5-yl)(3-(4-carboxylatophenylthio)-5-phenoxypyridin-2-yl)amide as a solid. To this salt was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.066 g, 0.35 mmol), 1-hydroxybenzotriazole hydrate (0.053 g, 0.35 mmol) in DMF (2 mL). N1,N1-dimethylethane-1,2-diamine (0.038 mL, 0.35 mmol) and DIEA (0.060 mL, 0.35 mmol) were added. The reaction stirred at 50° C. for 3 hours. The solution was then diluted with water, extracted with dichloromethane and concentrated. The crude material was purified via reverse phase HPLC to afford 4-(2-(3-(1-acetylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-phenoxypyridin-3-ylthio)-N-(2-(dimethylamino)ethyl)benzamide (0.064 g, 36% yield). 1H NMR (CDCl3) δ 1.76-1.88 (m, 2H), 2.04-2.12 (m 2H), 2.10 (s, 3H), 2.25 (s, 6H), 2.50 (t, 2H), 2.82 (t, 1H), 3.00-3.06 (m, 1H), 3.20 (t, 1H), 3.48 (dd, 2H), 3.87 (d, 1H), 4.54 (d, 1H), 6.80 (bs, 1H), 7.02 (d, 1H), 7.14-7.19 (m, 3H), 7.38 (t, 2H), 7.67 (d, 1H), 7.71 (d, 2H), 8.30 (d, 1H), 9.20 (bs, 1H).

Provenance & Evidence