Triethylamine → HCID 19369838, compound

HRID 849221Notes

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][CH2:23][C:24]([F:27])([F:26])[F:25])[C:15]=3[NH:14][C:13](=O)[C:12]=2[CH2:11][CH2:10]1.[CH2:29]([N:31](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][CH2:23][C:24]([F:25])([F:26])[F:27])[C:15]=3[N:14]=[C:13]([NH:31][CH3:29])[C:12]=2[CH2:11][CH2:10]1

Participants

Conditions

Temperature: -10 °C

Procedure

1-(2-Methyl-4-hydroxyphenyl)-4-oxo-6-β,β,β-trifluoroethoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline (2.5 g, 6.4 mmol) was dissolved in dichloromethane, triethylamine(2.2 ml, 16.0 mmol), and methanesulfonyl chloride(1.1 ml, 13.5 mmol) was added at -78° C. The reaction mixture was stirred for 3 hours, then slowly warmed up to -10° C., and stirred for 1 hours. The reaction mixture was extracted with dichloromethane, and 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 75% of yield.

Workup

stirringstirred for 1 hours
extractionThe reaction mixture was extracted 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-c606385ec69a45e08259558cfa672647
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011044

Reaction notes

Loading…