3-(6-Amino-5-methylpyridin-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)-3-methylpyridin-2-yl)urea

HRID 1271058Notes

Reaction equation

HRID 1271058 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][C:14]=1[CH3:33].C([O:36][C:37](=O)[NH:38][S:39]([C:42]1[S:43][C:44]([Cl:47])=[CH:45][CH:46]=1)(=[O:41])=[O:40])C>>[Cl:47][C:44]1[S:43][C:42]([S:39]([NH:38][C:37]([NH:12][C:13]2[C:14]([CH3:33])=[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:36])(=[O:41])=[O:40])=[CH:46][CH:45]=1

Participants

4

Reactant 3

HCID 184524893-(6-Amino-5-methylpyridin-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 116566071-(5-chlorothiophen-2-ylsulfonyl)-3-(5-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)-3-methylpyridin-2-yl)ureaYield 89.5%

Procedure

Analogous to the sulfonylurea urea formation described in Ex 5, 3-(6-amino-5-methylpyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.010 g, 0.034 mmol) and (5-Chloro-thiophene-2-sulfonyl)-carbamic acid ethyl ester (0.048 g, 0.166 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)-3-methylpyridin-2-yl)urea (0.016 g, 85%). RP-HPLC: 2.7 min; ES-MS (M+H)+=526.0; 1H-NMR (DMSO-d6) δ (ppm): 2.2 (s, 3), 2.8 (s, 3), 5.6 (s, 2), 6.2 (d, 1), 6.8 (bs, 1), 7.2 (s, 1), 7.4 (d, 1), 7.6 (s, 1), 7.8 (d, 1), 8.2 (d, 1), 9.6 (bs, 1).

Sources & evidence

ORD record
ord-0f320ea3fa7c40c59532c52362856c0c
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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