5-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid → 5-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (3H-imidazol-4-yl)-amide
Reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2.[N+:26]([C:29]1[N:30]=[CH:31][NH:32][CH:33]=1)([O-])=O>C(Cl)Cl.CO>[N:32]1[CH:33]=[C:29]([NH:26][C:23]([C:20]2[CH:21]=[CH:22][C:13]([C:3]3[C:4]([Cl:12])=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=3[Cl:1])=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[CH:15]3)=[O:24])[NH:30][CH:31]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
The title compound was prepared in analogy to the procedures described in Example 14 but using 5-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (Step 159.1), stirring the reaction mixture for 3 h at 70° C., and using 4-nitro-imidazole instead of 2-nitroimidazole in Step 14.3. The title compound: ESI-MS: 442.9 [M+H]+; tR=3.93 min (System 1); TLC: Rf=0.17 (DCM/MeOH/NH3aq, 94:5:1).
Workup
- customThe title compound was prepared in analogy to the procedures
Sources & evidence
- ORD record
- ord-46b4ec0b56034b34be46efdd5fc1a0a4
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536175B2
Reaction notes
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