Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 644079Generated: October 30, 2026

Pyrrolidine → 1-(Cyclohexyl)methyl-7-methoxy-3-{5-[(pyrrolidin-1-yl)methyl]-[1,3,4]-thiadiazol-2-yl}-1H-indole, hydrochloride salt

https://huagongshe.com/reaction/644079

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyrrolidineHCID 31268—
Reactant3-(5-chloromethyl-[1,3,4]thiadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indoleHCID 68702053—
SolventTetrahydrofuranHCID 8028—
Product1-(Cyclohexyl)methyl-7-methoxy-3-{5-[(pyrrolidin-1-yl)methyl]-[1,3,4]-thiadiazol-2-yl}-1H-indole, hydrochloride saltHCID 13172807740%

Reaction Steps

To a solution of 3-(5-chloromethyl-[1,3,4]thiadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole (93 mg, 0.25 mmol) in tetrahydrofuran was added pyrrolidine (0.101 ml, 1.235 mmol) and the mixture subjected to microwave irradiation at 150° C. for 5 minutes. The resulting reaction mixture was purified by flash column chromatography to give the title compound (42 mg, 0.1 mmol) as the free base. The free base was dissolved in dichloromethane and hydrogen chloride (1M solution in diethyl ether; 1 ml, 1 mmol) was added. The excess reagent and solvent were removed in vacuo to afford the title compound as a 1:1 hydrochloride salt.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07700634B2
Source datasetuspto-grants-2010_04
ORD IDord-88350d5249dc4614aeb2630dfa731e93
Source noteuspto-grants-2010_04