Diisopropylethylamine → HCID 12147065, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1)[NH2:5].C(N(CC)C(C)C)(C)C.Cl[C:34](Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl.[O:45]1[CH:49]=[CH:48][C:47]([NH2:50])=[N:46]1.C(=O)([O-])O.[Na+]>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:34]([NH:50][C:47]2[CH:48]=[CH:49][O:45][N:46]=2)=[O:36])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1Participants
Procedure
3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (20 mg) was dissolved in chlorobenzene (2 ml) and N,N-diisopropylethylamine (0.2 ml) to prepare a solution. A solution of triphosgene (18 mg) in chlorobenzene (0.5 ml) was then added to the solution, and the mixture was stirred at room temperature for 30 min. Next, 3-isoxazolamine (10 mg) was added thereto, and the mixture was further stirred at 110° C. overnight. The reaction solution was developed through diatomaceous earth impregnated with a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with chloroform. The solvent in the extract was removed by distillation. The residue was purified by HPLC using chloroform/methanol for development to give the title compound (2 mg, yield 8%).
Workup
- stirringthe mixture was further stirred at 110° C. overnight
- extractionfollowed by extraction with chloroform
- customThe solvent in the extract was removed by distillation
- customThe residue was purified by HPLC
Sources & evidence
- ORD record
- ord-bc9ecafbd05142e9b5ebe1d8f53e6e20
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07211587B2
Reaction notes
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