Methanol → HCID 22667112, compound
Reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][N:38]=1.CO>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[Br:43][C:40]1[CH:41]=[CH:42][C:37]([NH:36][C:28]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([O:9][C:10]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]=[CH:12][CH:11]=3)=[CH:8][C:2]=2[Cl:1])=[O:34])=[N:38][CH:39]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (122 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml), and a solution of triphosgene (110 mg) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 2-amino-5-bromopyridine (192 mg) was added to the reaction solution, and the mixture was stirred at room temperature for 2 hr. Methanol was added to the reaction solution, and the solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1) to give 108 mg (yield 55%) of the title compound.
Workup
- stirringthe mixture was stirred at room temperature for 2 hr
- customthe solvent was removed by distillation under the reduced pressure
- customThe residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1)
Sources & evidence
- ORD record
- ord-dd32804bed5947d9b2def119451aceed
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797823B1
Reaction notes
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