Dimethylformamide → 2',3'-Difluoro-5-(5-methyl-pyridin-2-yl)-biphenyl-3-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	L-Alaninol	HCID 80307	—
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	—
Product	2',3'-Difluoro-5-(5-methyl-pyridin-2-yl)-biphenyl-3-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide	HCID 45138253	—

Reaction Steps

A round bottom flask was charged with 2′,3′-difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylic acid (30.00 mg, 0.09222 mmol), (2S)-2-Aminopropan-1-ol (8.3119 mg, 0.11066 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.087662 g, 0.23055 mmol), N,N-diisopropylethylamine (0.064252 mL, 0.36888 mmol), N,N-dimethylformamide (0.157 mL, 2.03 mmol) and the reaction stirred over night at room temperature. The solvent was removed under reduced pressure and the residue purified by prep HPLC to get the compound as white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133122B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-9f6ccae33ed14d1995ab7cac63e583ba
Source note	uspto-grants-2015_09