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

HRID 1271059Notes

Reaction equation

HRID 1271059 reaction equation
NC(N)=O.S(=NC(N)=O)(=O)=O.[NH2:12][C:13]1[N:18]=[CH:17][C:16]([N:19]2[C:24](=[O:25])[C:23]3[CH:26]=[C:27]([F:32])[C:28]([NH:30][CH3:31])=[CH:29][C:22]=3[O:21][CH2:20]2)=[CH:15][CH:14]=1.[CH3:33][C:34]1[S:38][C:37]([S:39]([NH:42][C:43](=O)[O:44]CC)(=[O:41])=[O:40])=[CH:36][CH:35]=1>>[F:32][C:27]1[C:28]([NH:30][CH3:31])=[CH:29][C:22]2[O:21][CH2:20][N:19]([C:16]3[CH:15]=[CH:14][C:13]([NH:12][C:43]([NH:42][S:39]([C:37]4[S:38][C:34]([CH3:33])=[CH:35][CH:36]=4)(=[O:40])=[O:41])=[O:44])=[N:18][CH:17]=3)[C:24](=[O:25])[C:23]=2[CH:26]=1

Participants

4

Reactant 3

HCID 184524903-(6-Aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-oneHCID 18452516Ethyl 5-methylthiophen-2-ylsulfonylcarbamateHCID 86604073Sulfonylurea urea

Product 1

HCID 116631941-(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

Procedure

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).

Sources & evidence

ORD record
ord-5c0ce99847c14fc496445a60ae0a201f
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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