Diisopropylethylamine → 5-(2-Methoxyethoxy)-4'-methyl-N-((6-methylpyridin-3-yl)methyl)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	(6-Methylpyridin-3-yl)methanamine	HCID 12214337	—
Reactant	5-(2-Methoxyethoxy)-4'-methylbiphenyl-3-carboxylic acid	HCID 58187997	—
Solvent	Dimethylformamide	HCID 6228	—
Product	5-(2-Methoxyethoxy)-4'-methyl-N-((6-methylpyridin-3-yl)methyl)biphenyl-3-carboxamide	HCID 58188044	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of 5-(2-methoxyethoxy)-4′-methylbiphenyl-3-carboxylic acid (50 mg, 0.18 mmol) in N,N-dimethylformamide (1 mL) were added (6-methylpyridin-3-yl)methanamine (45 mg, 0.37 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (150 mg, 0.39 mmol) and N,N-diisopropylethylamine (150 μL, 0.86 mmol). The reaction mixture was stirred for 16 hours at 25° C. LC-MS indicated the reaction was complete. The reaction mixture was purified by preparative HPLC to afford the title product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946439B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-700750dbb27a46819c6c09a1fb2b182c
Source note	uspto-grants-2015_02