Diisopropylethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-(1-methyl-1H-indol-5-yl)-2-oxopyrrolidine-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	5-Chloro-1H-indole-3-ethylamine monohydrochloride	HCID 2827494	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	HCID 66831831	HCID 66831831	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-(1-methyl-1H-indol-5-yl)-2-oxopyrrolidine-3-carboxamide	HCID 66831944	21%

Reaction Steps

This compound was prepared according to method A with 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.055 g; 0.233 mmol), 1-(1-methylindolin-6-yl)-2-oxopyrrolidine-3-carboxylic acid (0.064 g; 0.245 mmol), HATU (0.091 g; 0.240 mmol) and N,N-diisopropylethylamine (0.101 mL; 0.583 mmol) in DMF (3 mL). The crude material was purified by flash chromatography on silica gel (eluent: 2 to 20% of ethyl acetate in dichloromethane) to give 0.021 g (21%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-(1-methyl-1H-indol-5-yl)-2-oxopyrrolidine-3-carboxamide as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434722B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-ef92e6caa3084a2db986f78ff38b25c5
Source note	uspto-grants-2016_09