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-methoxythiophen-2-ylsulfonyl)urea

Participants

Role	Name	HCID	Charge
Reactant	3-(6-Aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one	HCID 18452490	—
Reactant	3-Methoxy-5-methylthiophen-2-ylsulfonylcarbamate	HCID 18452491	—
Reactant	Sulfonylurea urea	HCID 86604073	—
Product	1-(5-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)pyridin-2-yl)-3-(5-methoxythiophen-2-ylsulfonyl)urea	HCID 11677829	—

Reaction Steps

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 3-methoxy-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-methoxythiophen-2-ylsulfonyl)urea. RP-HPLC: 2.7 min; ES-MS (M+H)+=508; 1H-NMR (DMSO-d6) δ (ppm): 2.8 (s, 3), 3.9 (s, 3), 5.6 (s, 2), 6.2 (d, 1), 6.5 (d, 1), 6.7 (d, 1), 7.4 (d, 1), 7.6 (d, 1), 7.8 (d, 1), 8.2 (s, 1), 9.4 (bs, 1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07205296B2
Source dataset	uspto-grants-2007_04
ORD ID	ord-9981cfeb781b41caa0d2385aeff147c9
Source note	uspto-grants-2007_04