Triethylamine → 2-(3-Methyl-1,2,4-oxadiazol-5-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
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-Methyl-1,2,4-oxadiazol-5-yl)benzoic acid	HCID 23146305	—
Reactant	(1S,2S)-1-N-[5-(Trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride	HCID 118308256	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(3-Methyl-1,2,4-oxadiazol-5-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide	HCID 118308053	—

Reaction Steps

A solution of 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid (CAS number 475105-77-2; 57.4 mg, 0.28 mmol), (1S,2S)-1-N-[5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 1; 72 mg, 0.26 mmol), HATU (146 mg, 0.38 mmol) and triethylamine (107 μl, 0.77 mmol) in dry DMF (852 μl) was stirred at room temperature for 72 hours. The reaction was diluted with DMSO and filtered through cotton wool before being purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09156829B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-c1dcbb6369bb4b2faec139440b4a0aad
Source note	uspto-grants-2015_10