Diisopropylethylamine → N3,4'-Dimethyl-N5-((6-methylpyridin-3-yl)methyl)-N3-(2,2,2-trifluoroethyl)biphenyl-3,5-dicarboxamide

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	Methyl(2,2,2-trifluoroethyl)amine hydrochloride	HCID 22496068	—
Reactant	4'-Methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)biphenyl-3-carboxylic acid	HCID 58188051	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N3,4'-Dimethyl-N5-((6-methylpyridin-3-yl)methyl)-N3-(2,2,2-trifluoroethyl)biphenyl-3,5-dicarboxamide	HCID 58188289	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of 4′-methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)biphenyl-3-carboxylic acid (50 mg, 0.14 mmol) in N,N-dimethylformamide (1.5 mL) were added 2,2,2-trifluoro-N-methylethanamine hydrochloride (60 mg, 0.40 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (120 mg, 0.32 mmol) and N,N-diisopropylethylamine (0.50 mL, 2.87 mmol). The reaction mixture was stirred for 16 hours at 25° C. The reaction mixture was purified by preparative HPLC to afford the final product as a light yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946439B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-83dddfa1dda64dfebed78c871870789c
Source note	uspto-grants-2015_02