Sodium hydride → N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-(methylsulfonyl)urea
Reaction equation
[H-].[Na+].[CH3:3][S:4]([NH-:7])(=[O:6])=[O:5].[C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][O:23][CH3:24])[N:16]=[CH:15][CH:14]=[C:13]2[O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=O)[O:34]C2C=CC=CC=2)=[CH:28][CH:27]=1)#[N:9]>O1CCCC1>[C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][O:23][CH3:24])[N:16]=[CH:15][CH:14]=[C:13]2[O:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:33]([NH:7][S:4]([CH3:3])(=[O:6])=[O:5])=[O:34])=[CH:30][CH:31]=1)#[N:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
After suspending sodium hydride (11 mg, 0.275 mmol) in tetrahydrofuran (8 ml) under a nitrogen atmosphere, methanesulfonylamide (31.4 mg, 0.330 mmol) was added while cooling in an ice water bath, and the mixture was stirred at room temperature for 10 minutes. Phenyl N-(4-(6-cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)carbamate (50 mg, 0.110 mmol) was added and the mixture was stirred at 60° C. for 1 hour. The insoluble portion was filtered off, and after concentration under reduced pressure, tetrahydrofuran-hexane (1:2) was added for crystallization to obtain the title compound (37.6 mg, 0.082 mmol, 75.0%) as gray crystals.
Workup
- temperaturewhile cooling in an ice water bath
- stirringthe mixture was stirred at 60° C. for 1 hour
- filtrationThe insoluble portion was filtered off
- concentrationafter concentration under reduced pressure, tetrahydrofuran-hexane (1:2)
- additionwas added for crystallization
Sources & evidence
- ORD record
- ord-d4ea104560a549fe9a05ff706431bf0f
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973160B2
Reaction notes
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