Diisopropylethylamine → HCID 68379549, compound

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)-1-methylpyridin-2(1H)-one hydrochloride	HCID 68379222	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 68379549	HCID 68379549	150.4%

Reaction Steps

A mixture of 4-(2-aminoethyl)-1-methylpyridin-2(1H)-one hydrochloride (76 mg, 0.4 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (100 mg, 0.4 mmol), HATU (190 mg, 0.5 mmol) and DIEA (260 mg, 2 mmol) in 25 mL of DCM and 5 mL of DMF was stirred at room temperature overnight. The solution was washed with sat NaHCO3 (2×20 mL), brine (2×20 mL), dried over anhydrous sodium sulfate, concentrated under reduce pressure to give crude N-(2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (230 mg) and used for next step without further purification. LC-MS: 383 [M+H]+, tR=1.41 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08921383B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-92db1e8d120d436596d664df15ec9568
Source note	uspto-grants-2014_12