Diisopropylethylamine → 5-(Hydroxy(phenyl)methyl)-4'-methyl-N-((R)-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	5-(Hydroxy(phenyl)methyl)-4'-methylbiphenyl-3-carboxylic acid	HCID 58187984	—
Reactant	(R)-1-(6-Methylpyridin-3-yl)ethan-1-amine dihydrochloride	HCID 67053782	—
Solvent	Dimethylformamide	HCID 6228	—
Product	5-(Hydroxy(phenyl)methyl)-4'-methyl-N-((R)-1-(6-methylpyridin-3-yl)ethyl)biphenyl-3-carboxamide	HCID 58188024	—

Reaction Conditions

Temperature	30 °C

Reaction Steps

To a solution of 5-(hydroxy(phenyl)methyl)-4′-methylbiphenyl-3-carboxylic acid (50 mg, 0.16 mmol) in N,N-dimethylformamide (1 mL) were added (R)-1-(6-methylpyridin-3-yl)ethanamine dihydrochloride (70 mg, 0.34 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (120 mg, 0.32 mmol) and N,N-diisopropylethylamine (500 μL, 2.87 mmol). The reaction mixture was stirred for 16 hours at 30° C. The reaction mixture was purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[1 mM Et2NH]) to afford 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-1f3a2e2dcc8d43d3b76dfcef64c16977
Source note	uspto-grants-2015_02