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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2275097Generated: November 2, 2026

Trifluoroacetic acid → N-[2-(3-Cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yloxy)-ethyl]-methanesulfonamide

https://huagongshe.com/reaction/2275097

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantMethanesulfonyl chlorideHCID 31297—
ReactantDiisopropylethylamineHCID 81531—
Reactant8-(2-amino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 66833792—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
ProductN-[2-(3-Cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yloxy)-ethyl]-methanesulfonamideHCID 6683385029%

Reaction Steps

Trifluoroacetic acid salt of 8-(2-amino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A8-2, 19 mg, 0.044 mmol) was suspended in dichloromethane (0.5 mL), added with diisopropylethylamine (0.0157 mL, 2 eq.) and methanesulfonyl chloride (0.0034 mL, 1 eq.), and then stirred at room temperature for 2 hr. The reaction solution was added to water, and then extracted with dichloromethane. After washing with saturated brine, the organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were separated by silica gel preparative TLC (ethyl acetate 100%) to obtain the target compound (5.5 mg, 29%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09126931B2
Source datasetuspto-grants-2015_09
ORD IDord-c53f95b123eb41a28f76113c53f91492
Source noteuspto-grants-2015_09