1,2-Dibromoethane → HCID 66788866, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([NH:10][S:11]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])(=[O:13])=[O:12])[C:7]([OH:23])=[C:6]([Cl:24])[CH:5]=1.Br[CH2:27][CH2:28]Br>>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([Cl:24])[C:7]2[O:23][CH2:28][CH2:27][N:10]([S:11]([C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=3[O:21][CH3:22])(=[O:13])=[O:12])[C:8]=2[CH:9]=1)=[O:25]Participants
Procedure
The title compound, MS (ISP)=534.8 (M−H)−, was produced in analogy with example 36, steps 1-4. Step 1 was performed using 3-chloro-5-(5-chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl ester (example 50, step 2) and 1,2-dibromoethane, yielding 8-chloro-4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester, which was hydrolyzed in step 2 to afford 8-chloro-4-(5-chloro-2-methoxybenzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid. This was reacted with ethyl 4-aminobenzoate in step 3 to produce 4-{[8-chloro-4-(5-chloro-2-methoxy-benzenesulfonyl)-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-025ab373b4eb42018e20f9938405a8a8
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030308B2
Reaction notes
Loading…