Diisopropylethylamine → 2-(3-chloropyrazin-2-yl)-N-(2-(3-methoxyphenyl)cyclopropyl)-2-methylpropanamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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	2-(3-Methoxyphenyl)cyclopropan-1-amine	HCID 13972236	—
Reactant	2-(3-Chloropyrazin-2-yl)-2-methylpropanoic acid	HCID 86694118	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-(3-chloropyrazin-2-yl)-N-(2-(3-methoxyphenyl)cyclopropyl)-2-methylpropanamide	HCID 86694244	53.1%

Reaction Steps

A mixture of Intermediate 29 (0.2 g, 0.997 mmol), 2-(3-methoxyphenyl)cyclopropanamine (FSSI, mixture of cis/trans, 0.163 g, 0.997 mmol), HATU (GenScript Corporation, 0.455 g, 1.196 mmol), hunig's base (Aldrich, 0.696 ml, 3.99 mmol) in DMF (0.997 ml) and DCM (0.997 ml) was stirred at room temperature overnight. Reaction mixture was diluted with DCM and washed with water and brine. The organic layer was loaded onto a Biotage samplet (25 g). Purification (0-100% EtOAc/hexane) produced 2-(3-chloropyrazin-2-yl)-N-(2-(3-methoxyphenyl)cyclopropyl)-2-methylpropanamide (0.183 g, 0.529 mmol, 53%). M+1: 346.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09174992B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-2bfe9631baeb4560a0fa045cd02a9cd3
Source note	uspto-grants-2015_11