Diisopropylethylamine → 4'-Methyl-N-((R)-1-(2-methylpyrimidin-5-yl)ethyl)-5-(octahydropyrrolo[1,2-a]pyrazine-2-carbonyl)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-(octahydropyrrolo[1,2-a]pyrazine-2-carbonyl)biphenyl-3-carboxylic acid	HCID 58188156	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4'-Methyl-N-((R)-1-(2-methylpyrimidin-5-yl)ethyl)-5-(octahydropyrrolo[1,2-a]pyrazine-2-carbonyl)biphenyl-3-carboxamide	HCID 58188014	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of 4′-methyl-5-(octahydropyrrolo[1,2-a]pyrazine-2-carbonyl)biphenyl-3-carboxylic acid (50 mg, 0.14 mmol) in N,N-dimethylformamide (1.0 mL) were added (R)-1-(2-methylpyrimidin-5-yl)ethanamine (35 mg, 0.25 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (120 mg, 0.32 mmol) and N,N-diisopropylethylamine (120 μL, 0.69 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-955a48c0550543a5b750961730a45bf7
Source note	uspto-grants-2015_02