Diisopropylethylamine → (R)-N3-Isobutyl-N3,4'-dimethyl-N5-(1-(2-methylpyrimidin-5-yl)ethyl)biphenyl-3,5-dicarboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	(R)-1-(2-Methyl-5-pyrimidinyl)ethanamine	HCID 55281681	—
Reactant	5-(Isobutyl(methyl)carbamoyl)-4'-methylbiphenyl-3-carboxylic acid	HCID 58188089	—
Solvent	Dichloromethane	HCID 6344	—
Product	(R)-N3-Isobutyl-N3,4'-dimethyl-N5-(1-(2-methylpyrimidin-5-yl)ethyl)biphenyl-3,5-dicarboxamide	HCID 58188066	—

Reaction Steps

To a mixture of 5-(isobutyl(methyl)carbamoyl)-4′-methylbiphenyl-3-carboxylic acid (15 mg, 0.046 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (18 mg, 0.092 mmol), 1-hydroxybenzotriazole hydrate (7.0 mg, 0.046 mmol), and CH2Cl2 (2 mL) were added (R)-1-(2-methylpyrimidin-5-yl)ethanamine (9.5 mg, 0.069 mmol) (WO 2008/130481) and N,N-diisopropylethylamine (12 μL, 0.069 mmol). The mixture was stirred at room temperature overnight, and then concentrated in vacuo. The residue was purified by preparative HPLC (100×21.2 mm C18 column, 40-70% MeCN/water[10 mM Et2NH]) to afford a white foam.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946439B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-80f4d51820284b4f90e077c0dee3b5cc
Source note	uspto-grants-2015_02