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

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Analogous to the sulfonylurea urea coupling method described in Ex 5, 3-(6-aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one was coupled with ethyl 5-methylthiophen-2-ylsulfonylcarbamate to yield 1-(5-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)pyridin-2-yl)-3-(5-methylthiophen -2-ylsulfonyl)urea. RP-HPLC: 2.7 min; ES-MS (M+H)+=492.3; 1H-NMR (MeOH-d4) δ (ppm): 2.5 (s, 3), 2.86 (s, 3), 5.5 (s, 2), 6.2 (d, 1), 6.8 (d, 1), 7.4 (d, 1), 7.46 (d, 1), 7.6 (d, 1), 7.8 (dd, 1), 8.3 (d, 1).

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