1,2-Dibromoethane → 4-(5-chloro-2-methoxy-benzenesulfonyl)-8-trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester

HRID 1360282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360282
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:7]([OH:14])=[C:6]([NH:15][S:16]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])(=[O:18])=[O:17])[CH:5]=1.Br[CH2:30][CH2:31]Br>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:13])[F:12])[C:7]2[O:14][CH2:31][CH2:30][N:15]([S:16]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=3[O:26][CH3:27])(=[O:18])=[O:17])[C:6]=2[CH:5]=1)=[O:28]

Komponenten

3

Edukt 2

HCID 78391,2-DibromoethaneHCID 667886743-(5-Chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-5-trifluoromethyl-benzoic acid methyl ester

Produkt 1

HCID 667894324-(5-chloro-2-methoxy-benzenesulfonyl)-8-trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester

Versuchsvorschrift

The title compound, MS (ISP)=569.0 (M−H)−, was produced in analogy with example 36, steps 1-4. Step 1 was performed using 3-(5-chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-5-trifluoromethyl-benzoic acid methyl ester (example 40, step 2) and 1,2-dibromoethane, yielding 4-(5-chloro-2-methoxy-benzenesulfonyl)-8-trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester, which was hydrolyzed in step 2 to afford 4-(5-chloro-2-methoxy-benzenesulfonyl)-8-trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid. This was reacted with ethyl 4-aminobenzoate in step 3 to produce 4-{[4-(5-chloro-2-methoxy-benzenesulfonyl)-8-trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid ethyl ester, which was hydrolyzed in step 4.

Quellen und Nachweise

ORD-Eintrag
ord-5137fc38c85040428ccea955278cab44
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879845B2

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