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

HRID 1271060Notes

Reaction equation

HRID 1271060 reaction equation
N[C:2](N)=[O:3].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.CO[C:35]1[CH:39]=[C:38](C)[S:37][C:36]=1[S:41]([NH:44][C:45](=[O:47])[O-])(=[O:43])=[O:42]>>[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:45]([NH:44][S:41]([C:36]4[S:37][C:38]([O:3][CH3:2])=[CH:39][CH:35]=4)(=[O:42])=[O:43])=[O:47])=[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 184524913-Methoxy-5-methylthiophen-2-ylsulfonylcarbamateHCID 86604073Sulfonylurea urea

Product 1

HCID 116778291-(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

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 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).

Sources & evidence

ORD record
ord-9981cfeb781b41caa0d2385aeff147c9
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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