Diisopropylethylamine → N2-[(1S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl]-N1-(l-cyanocyclopropyl)-L-leucinamide

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	1-Amino-1-cyclopropanecarbonitrile hydrochloride	HCID 14586363	—
Reactant	N-[(1S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl]-L-leucine	HCID 86590542	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N2-[(1S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl]-N1-(l-cyanocyclopropyl)-L-leucinamide	HCID 59715496	—

Reaction Steps

To a solution of the crude acid (0.73 g, 2.25 mmol) from Step 2 in DMF (12 mL) was added 1-aminocyclopropanecarbonitrile hydrochloride (0.4 g, 3.37 mmol.) and HATU (0.86 g, 2.25 mmol). Diisopropylethylamine (1.96 mL, 11.24 mmol) was added, the mixture was stirred at rt for 20 h. EtOAc and water were added. The mixture was separated after agitation and the organic extract was washed with water and brine and dried over anhyd. MgSO4. Concentration of the organic extract followed by chromatography (30-50% EtOAc/hexane) gave the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08318748B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-ac562651857c47c38a28f094eb3fac7f
Source note	uspto-grants-2012_11