Diisopropylethylamine → N-(2-(2-oxo-1,2-dihydropyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid	HCID 2734621	—
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	4-(2-aminoethyl)pyridin-2(1H)-one hydrobromide	HCID 68379399	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(2-(2-oxo-1,2-dihydropyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide	HCID 68379400	108.6%

Reaction Steps

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (100 mg, 0.4 mmol), 4-(2-aminoethyl)pyridin-2(1H)-one hydrobromide (96 mg, 0.44 mmol), HATU (182 mg, 0.48 mmol) and DIEA (155 mg, 1.20 mmol) in 30 mL of DCM was stirred at room temperature overnight. The solution was washed with sat NaHCO3 (2×30 mL), brine (30 mL), dried over anhydrous sodium sulfate, concentrated under reduce pressure to give crude N-(2-(2-oxo-1,2-dihydropyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (160 mg) and used without further purification. LC-MS: 369 [M+H]+, tR=1.35 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08921383B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-a159f2305c2c4394908e642eca0d64cf
Source note	uspto-grants-2014_12