Diisopropylethylamine → 2'-Cyano-4'-methyl-N-((R)-1-(6-methylpyridin-3-yl)ethyl)-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxamide

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'-Cyano-4'-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylic acid	HCID 58188084	—
Reactant	(R)-1-(6-Methylpyridin-3-yl)ethan-1-amine dihydrochloride	HCID 67053782	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2'-Cyano-4'-methyl-N-((R)-1-(6-methylpyridin-3-yl)ethyl)-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxamide	HCID 58187948	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of 2′-cyano-4′-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylic acid (32 mg, 0.095 mmol) in N,N-dimethylformamide (1 mL) were added (R)-1-(6-methylpyridin-3-yl)ethanamine dihydrochloride (50 mg, 0.24 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (100 mg, 0.26 mmol), and N,N-diisopropylethylamine (300 μL, 1.72 mmol). The reaction mixture was stirred for 16 hours at 25° C., and then purified by preparative HPLC to afford the final product as a light color solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946439B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-0a51ba782dfb44ae90f214762b7aef5f
Source note	uspto-grants-2015_02