Ammonium Chloride → 5-{[6-(2-Hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide

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5-{[6-(2-Hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid (64 mg, 0.13 mmol), N-hydroxybenzotriazole (39 mg, 0.25 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (48 mg, 0.25 mmol), and ammonium chloride (34 mg, 0.63 mmol) were taken up in DMF (4.2 mL) under argon. Diisopropylethylamine (110 μl, 0.63 mmol) was added and the mixture was stirred at room temperature for 36 hours. The solution was then diluted with water to precipitate a white solid that was collected by filtration, washed with water and dried under reduced pressure to afford the title compound as a bright yellow solid. 1H NMR (500 MHz, d6-DMSO): δ 11.21 (s, 1H), 8.66 (d, 1H), 8.08 (dd, 1H), 7.72 (s, 1H), 7.69 (t, 1H), 7.59 (s, 1H), 7.05 (d, 1H), 6.96 (d, 1H), 6.93 (d, 1H), 4.53 (m, 1H), 3.99 (m, 2H), 3.69 (m, 5H), 3.55 (m, 8H), 2.50 (m, 4H). LRMS (APCI) calc'd for C24H30N7O4S [M+H]+ 512.2, found 512.1

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