Ammonia → 2-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)acetamide

Participants

Reaction Conditions

Reaction Steps

EDC.HCl (85.8 mg, 0.37 mmol), HOBt (49.4 mg, 0.37 mmol), and DMAP (cat.) were sequentially added to a solution of 2-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)acetic acid (100 mg, 0.24 mmol, Example 49) and pyridine (10 mL). After 5 min, a saturated solution of ammonia in THF (10 mL) was added, and the reaction was heated at 40° C. overnight. The reaction was allowed to cool to rt, concentrated to remove THF, and then 2N HCl was added to pH=3. The precipitate was filtered, washed with water, and dried. The crude product was refluxed in ethyl acetate (20 mg/mL) for 10 min, sonicated to break up large particles, refluxed for another 10 min, and then let stand overnight. Filtration and drying gave 2-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)acetamide: 1H NMR (400 MHz, DMSO-d6): δ 9.58 (br s, 1H), 8.79 (s, 2H), 7.97 (d, 1H), 7.57 (s, 1H), 7.41 (s, 1H), 7.23 (d, 1H), 4.62 (s, 1H), 4.40 (s, 2H), 3.94 (s, 3H); MS (ESI): 409.8.

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