Diisopropylethylamine → (R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-(5-bromo-4-cyano-2-fluorophenylamino)propanamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Bromo-4,5-difluorobenzonitrile	HCID 19261277	—
Reactant	(R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-aminopropanamide	HCID 67516322	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	(R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-(5-bromo-4-cyano-2-fluorophenylamino)propanamide	HCID 67514927	31.7%

Reaction Steps

A solution of 2-bromo-4,5-difluorobenzonitrile (100 mg, 0.458 mmol), ((R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-aminopropanamide (100 mg, 0.434 mmol) and DIEA (0.100 mL, 0.575 mmol) in DMSO (3 mL) was stirred at 120 C for 18 h. The mixture was purified by HPLC to give (R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-(5-bromo-4-cyano-2-fluorophenylamino)propanamide (59 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846928B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-81adb1500b354bd5b4cb95dc9e973c1f
Source note	uspto-grants-2014_09