3-(6-Aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one → 1-(5-chlorothiophen-2-ylsulfonyl)-3-(5-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)pyridin-2-yl)urea

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Analogous to the sulfonylurea urea formation described in Ex 5, 3-(6-aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.017 g, 0.058 mmol) and (5-Chloro-thiophene-2-sulfonyl)-carbamic acid ethyl ester (0.026 g, 0.096 mmol) were coupled to give 1-(5-chlorothiophen-2-ylsulfonyl)-3-(5-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)pyridin-2-yl)urea (0.007 g, 24%). RP-HPLC: 2.7 min; ES-MS (M+H)+=512.0; 1H-NMR (MeOH-d4) δ (ppm): 2.82 (s, 3), 5.4 (s, 2), 6.2 (d, 1), 6.9 (d, 1), 7.3 (d, 1), 7.6 (dd, 1), 8.0 (d, 1), 8.1 (d, 1).

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