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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1408311Generated: November 3, 2026

Trifluoroacetic acid → 13-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

https://huagongshe.com/reaction/1408311

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactant10-tert-butyl 6-methyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylateHCID 59837558—
SolventDichloromethaneHCID 6344—
Product13-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acidHCID 5755909896.8%

Reaction Steps

13-Cyclohexyl-3-methoxy-7H-benzo[3,4]azepino[1,2-a]indole-6,10-dicarboxylic acid 10-tert-butyl ester 6-methyl ester 1a (1 g, 1 eq) was dissolved in dry dichloromethane under N2, followed by the addition of trifluoroacetic acid (TFA) (8.88 ml, 60 eq). The solution was stirred at RT for 24 h. The solvent was then removed under reduced pressure. The crude product was triturated with diethyl ether. The crystals were filtered off and dried under vacuum overnight to afford the title product 13-Cyclohexyl-3-methoxy-7H-benzo[3,4]azepino[1,2-a]indole-6,10-dicarboxylic acid 6-methyl ester 13a (89%, 0.86 g); LC-MS: Rt. 3.19 min., m/z 446 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08921355B2
Source datasetuspto-grants-2014_12
ORD IDord-31b29ca9a3214ddf916b49d91d9c5086
Source noteuspto-grants-2014_12