Diisopropylethylamine → (R)-2',3'-difluoro-5-(5-methylpyridin-2-yl)-N-(1-morpholinopropan-2-yl)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',3'-Difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylic acid	HCID 58449360	—
Reactant	(R)-1-Morpholinopropan-2-amine hydrochloride	HCID 67310127	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(R)-2',3'-difluoro-5-(5-methylpyridin-2-yl)-N-(1-morpholinopropan-2-yl)biphenyl-3-carboxamide	HCID 45138400	—

Reaction Steps

A round bottom flask was charged with 2′,3′-difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylic acid (30 mg, 0.092 mmol), (R)-1-morpholinopropan-2-amine hydrochloride (20 mg, 0.11 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (88 mg, 0.23 mmol), N,N-diisopropylethylamine (64 μL, 0.37 mmol), N,N-dimethylformamide (0.5 mL) and the reaction was stirred overnight at room temperature. The mixture was purified by HPLC to afford the title compound as a light orange solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133122B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-d7e385d7f3464226bb8a7d374d415a08
Source note	uspto-grants-2015_09