Triethylamine → HCID 19369820, compound

HRID 849197Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

1-(2-Methyl-4-hydroxyphenyl)-4-oxo-6-trifluoromethoxy-2,3,4,5-tetra-hydropyrrolo[3,2-c]quinoline(2.3g, 6.1 mmol) was dissolved in dichloromethane. Triethylamine(2.6 ml, 18.0 mmol) was added and methanesulfonyl chloride(1.0 ml, 12.8 mmol) were added, and then the reaction mixture was stirred at -78° C. for 3 hours. The reaction mixture was slowly warmed up to -10° C., and stirred for 1 hours. After extracting the reaction mixture with dichloromethane, the organic layer was washed with water for 3 times. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized in dichloromethane/hexane to obtain 2.3 g of desired compound as solid in 72% of yield.

Workup

temperatureThe reaction mixture was slowly warmed up to -10° C.
stirringstirred for 1 hours
extractionAfter extracting the reaction mixture with dichloromethane
washthe organic layer was washed with water for 3 times
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was crystallized in dichloromethane/hexane

Sources & evidence

ORD record: ord-e824279267f541118c05e6b3cea34172
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011044

Reaction notes

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