Diisopropylethylamine → 2,6-dichloro-N-(2-((1R,2R)-2-chlorocyclopropanecarboxamido)pyridin-4-yl)benzamide

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	2-Chlorocyclopropane-1-carboxylic acid	HCID 13399523	—
Reactant	N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide	HCID 59618313	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2,6-dichloro-N-(2-((1R,2R)-2-chlorocyclopropanecarboxamido)pyridin-4-yl)benzamide	HCID 59618025	12%

Reaction Conditions

Temperature	110 °C

Reaction Steps

To a solution of N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (150 mg, 0.54 mmol), 2-chlorocyclopropanecarboxylic acid (66 mg, 0.54 mmol) and HATU (381 mg, 1.08 mmol) in dry DMF (4.5 mL) was added DIPEA (144 mg, 1.08 mmol). The mixture was stirred at 110° C. in a microwave reactor for 1 hour. The mixture was cooled to room temperature and diluted with EtOAc (30 mL). The organic solution was washed with water (10 mL) and brine (10 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give the desired compounds.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08486950B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-0b50e7736efd4c7bac27045464ccb921
Source note	uspto-grants-2013_07