1-Sulfonylurea → 1-(5-chlorothiophen-2-ylsulfonyl)-3-(4-(6-chloro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)phenyl)urea

HRID 1271062Notes

Reaction equation

HRID 1271062 reaction equation
S(=NC(N)=O)(=O)=O.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:20](=[O:21])[C:19]3[CH:22]=[C:23]([Cl:28])[C:24]([NH:26][CH3:27])=[CH:25][C:18]=3[O:17][CH2:16]2)=[CH:11][CH:10]=1.C([O:31][C:32](=O)[NH:33][S:34]([C:37]1[S:38][C:39]([Cl:42])=[CH:40][CH:41]=1)(=[O:36])=[O:35])C>>[Cl:42][C:39]1[S:38][C:37]([S:34]([NH:33][C:32]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([N:15]3[C:20](=[O:21])[C:19]4[CH:22]=[C:23]([Cl:28])[C:24]([NH:26][CH3:27])=[CH:25][C:18]=4[O:17][CH2:16]3)=[CH:13][CH:14]=2)=[O:31])(=[O:36])=[O:35])=[CH:41][CH:40]=1

Participants

4

Reactant 3

HCID 118190831-SulfonylureaHCID 184524853-(4-Aminophenyl)-6-chloro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-oneHCID 24778122Ethyl ((5-chlorothiophen-2-yl)sulfonyl)carbamate

Product 1

HCID 117063741-(5-chlorothiophen-2-ylsulfonyl)-3-(4-(6-chloro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)phenyl)urea

Procedure

Analogues to the sulfonylurea formation described in Ex. 5, 3-(4-aminophenyl)-6-chloro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (Ex. 47) (44 mg, 0.15 mmol) and (5-Chloro-thiophene-2-sulfonyl)-carbamic acid ethyl ester (59 mg, 0.22 mmol) were coupled to give 1-(5-chlorothiophen-2-ylsulfonyl)-3-(4-(6-chloro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)phenyl)urea. RP-HPLC: 2.70 min; ES-MS (M+H)+=528.0; 1H-NMR (MeOH-d4) δ (ppm): 2.8 (s, 3), 5.4 (s, 2), 6.2 (s, 1), 6.9 (d, 1), 7.1 (d, 2), 7.39 (d, 1), 7.48 (d, 2), 7.7 (s, 1).

Sources & evidence

ORD record
ord-6b55a759d97e4a738e789fdbaaa3fdea
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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