1,2-Dibromoethane → HCID 66789882, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[C:6]([NH:12][S:13]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])(=[O:15])=[O:14])[CH:5]=1.Br[CH2:27][CH2:28]Br>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([CH3:10])[C:7]2[O:11][CH2:28][CH2:27][N:12]([S:13]([C:16]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=3[O:23][CH3:24])(=[O:15])=[O:14])[C:6]=2[CH:5]=1)=[O:25]Participants
Procedure
The title compound, MS (ISP)=514.9 (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-methyl-benzoic acid methyl ester (example 52, step 2) and 1,2-dibromoethane, yielding 4-(5-chloro-2-methoxy-benzenesulfonyl)-8-methyl-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-methyl-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-methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid ethyl ester, which was hydrolyzed in step 4.
Sources & evidence
- ORD record
- ord-f05bbc0e93f843a9b50b055d2fe098b4
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030308B2
Reaction notes
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