Dibutyltin oxide → 8-(5-(2H-tetrazol-5-yl)pentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

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A mixture of 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanenitrile (170 mg, 0.38 mmol, Example 57), dibutyltin oxide (100 mg, 0.4 mmol), TMSN3 (0.5 mL, 3.8 mmol), and anhydrous toluene (5 mL) was heated at 110° C. under N2 for 15.5 h, allowed to cool to rt, and then quenched with methanol (1 mL). The reaction was concentrated and purified by silica gel chromatography (1:0→4:1; dichloromethane:methanol) to give 8-(5-(2H-tetrazol-5-yl)pentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.51 (br s, 1H), 8.81 (s, 2H), 7.94 (d, 1H), 7.20 (d, 1H), 4.63 (s, 1H), 3.98 (t, 2H), 3.90 (s, 3H), 2.89 (t, 2H), 1.80-1.65 (m, 4H), 1.51 (m, 2H); MS (ESI): 490.9.

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