Triethylamine → HCID 24853027, compound

HRID 2388086Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH2:19])[CH:5]=[N:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[S:28](Cl)(=[O:30])=[O:29].C(N([CH2:37][CH3:38])CC)C>ClCCl>[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[S:28]([N:19]([S:28]([C:38]1[CH:37]=[CH:22][C:21]([Cl:20])=[CH:26][C:25]=1[Cl:27])(=[O:30])=[O:29])[C:4]1[CH:5]=[N:6][C:7]([O:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:2]([Cl:1])[CH:3]=1)(=[O:30])=[O:29]

Participants

Conditions

Temperature: 45 °C

Procedure

Dry dichloromethane (15 mL) was added to 5-Chloro-6-(quinolin-3-yloxy)-pyridin-3-yl amine (250 mg, 1 mmol) obtained in preparation 1. To the stirred solution was added 2,4-dichlorobenzenesulfonyl chloride (492 mg, 2.2 mmol) followed by the addition of triethylamine (2.2 mmol). The reaction mixture was then maintained at 45° C. for 15 hours, cooled to room temperature (25° C.) and diluted with dichloromethane. The dichloromethane layer was washed with water, dried over sodium sulfate and concentrated under vacuum to get the crude, which was further purified by column chromatography (silica gel).

Workup

customobtained in preparation 1
temperaturecooled to room temperature (25° C.)
washThe dichloromethane layer was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum
customto get the crude, which
customwas further purified by column chromatography (silica gel)

Sources & evidence

ORD record: ord-298b7e01ef58444a9d30c9ce6bd0e53c
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269010B2

Reaction notes

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