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

HRID 1271055Notes

Reaction equation

HRID 1271055 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.C([O:35][C:36](=O)[NH:37][S:38]([C:41]1[S:42][C:43]([Cl:46])=[CH:44][CH:45]=1)(=[O:40])=[O:39])C>>[Cl:46][C:43]1[S:42][C:41]([S:38]([NH:37][C:36]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([N:19]3[C:24](=[O:25])[C:23]4[CH:26]=[C:27]([F:32])[C:28]([NH:30][CH3:31])=[CH:29][C:22]=4[O:21][CH2:20]3)=[CH:17][N:18]=2)=[O:35])(=[O:40])=[O:39])=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 184524903-(6-Aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-oneHCID 24778122Ethyl ((5-chlorothiophen-2-yl)sulfonyl)carbamateHCID 86604073Sulfonylurea urea

Product 1

HCID 115915881-(5-chlorothiophen-2-ylsulfonyl)-3-(5-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)pyridin-2-yl)ureaYield 24%

Procedure

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).

Sources & evidence

ORD record
ord-4f148b60ae524eb28cbbb186cf2426ba
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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