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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 15487Generated: October 30, 2026

Benzenesulfonyl chloride → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-[bis(phenylsulfonyl)amino]-1-benzothiophene-2-carboxamide hydrochloride

https://huagongshe.com/reaction/15487

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzenesulfonyl chlorideHCID 7369—
ReactantTriethylamineHCID 8471—
ReactantN-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-amino-1-benzothiophene-2-carboxamide hydrochlorideHCID 68432473—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventDimethylformamideHCID 6228—
ProductN-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-[bis(phenylsulfonyl)amino]-1-benzothiophene-2-carboxamide hydrochlorideHCID 68431062—

Reaction Steps

40 mg (0.11 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-amino-1-benzo-thiophene-2-carboxamide hydrochloride are dissolved in 2 ml of DMF, 6.5 mg (0.05 mmol) of N,N-dimethyl-4-aminopyridine, 59.6 μl (0.43 mmol) of triethylamine and 27.2 μl (0.21 mmol) of benzenesulfonyl chloride are added and the mixture is stirred at room temperature for 16 h. The reaction mixture is purified by preparative HPLC. The product is dissolved in a mixture of 1N aqueous hydrochloric acid and acetonitrile, then again concentrated and dried under high vacuum. 33 mg (50% of theory) of the title compound are obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07732477B2
Source datasetuspto-grants-2010_06
ORD IDord-c321650a146b4d30abed589864c0cf3c
Source noteuspto-grants-2010_06