Diisopropylethylamine → (R)-2'-Cyano-5-(hydroxymethyl)-4'-methyl-N-(1-(6-methylpyridin-3-yl)ethyl)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-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylic acid	HCID 58188342	—
Reactant	(R)-1-(6-Methylpyridin-3-yl)ethan-1-amine dihydrochloride	HCID 67053782	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(R)-2'-Cyano-5-(hydroxymethyl)-4'-methyl-N-(1-(6-methylpyridin-3-yl)ethyl)biphenyl-3-carboxamide	HCID 58188168	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a stirred solution of 2′-cyano-5-(hydroxymethyl)-4′-methylbiphenyl-3-carboxylic acid (40 mg, 0.15 mmol) in N,N-dimethylformamide (1 mL) were added (R)-1-(6-methylpyridin-3-yl)ethanamine dihydrochloride (60 mg, 0.29 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (120 mg, 0.32 mmol), and N,N-diisopropylethylamine (400 μL, 2.3 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-5e8cae9ea22a466f8f0c51c32387f7e0
Source note	uspto-grants-2015_02