Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 880310Generated: October 30, 2026

Triethylamine → tert-butyl(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)carbamoyl)phenyl)carbamate

https://huagongshe.com/reaction/880310

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant3-(((Tert-butoxy)carbonyl)amino)benzoic acidHCID 854162—
Reactant1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olHCID 16790720—
SolventDichloromethaneHCID 6344—
Producttert-butyl(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)carbamoyl)phenyl)carbamateHCID 9024549971.6%

Reaction Conditions

Temperature25 °C

Reaction Steps

To a solution of 3-((tert-butoxycarbonyl)amino)benzoic acid (2.5 g, 10.5 mmol) in DCM (25 mL) was added EDCI (3.0 g, 15.7 mmol), HOBt (2.1 g, 15.7 mmol), Et3N (2.1 g, 21 mmol) and 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (2.2 g, 10.5 mmol). The mixture was stirred at 25° C. for 16 h. The reaction solution was washed with water and extracted with DCM. The organic layer was concentrated, and the residue was purified by column chromatography to give the title product (3.2 g, Yield 71%). LCMS (m/z): 426.3 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08993555B2
Source datasetuspto-grants-2015_03
ORD IDord-e3a4f561450b4a0b8be013bce385962b
Source noteuspto-grants-2015_03