Diisopropylethylamine → (R)-4'-Methyl-N-(1-(2-methylpyrimidin-5-yl)ethyl)-5-(thiazol-2-yloxy)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	(R)-1-(2-Methyl-5-pyrimidinyl)ethanamine	HCID 55281681	—
Reactant	4'-Methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylic acid	HCID 58188071	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(R)-4'-Methyl-N-(1-(2-methylpyrimidin-5-yl)ethyl)-5-(thiazol-2-yloxy)biphenyl-3-carboxamide	HCID 58188035	—

Reaction Steps

To a solution of 4′-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylic acid (50 mg, 0.16 mmol) in N,N-dimethylformamide (1 mL) were added (R)-1-(2-methylpyrimidin-5-yl)ethanamine (45 mg, 0.33 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (150 mg, 0.39 mmol) and N,N-diisopropylethylamine (200 μL, 1.15 mmol). The reaction mixture was stirred at room temperature for 16 hours. LC-MS indicated the reaction was complete. The reaction mixture was purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 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-231ef48f674c4c36b3c80445fb0acabc
Source note	uspto-grants-2015_02