Diisopropylethylamine → HCID 66586978, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-(tert-Butoxycarbonyl)benzoic acid	HCID 2760951	—
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	HCID 66586798	HCID 66586798	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 66586978	HCID 66586978	95.3%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a mixture of 2-(2-amino-5-(diethylamino)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide (25a, 6.33 mmol, 2.8 g), 3-(tert-butoxycarbonyl)benzoic acid (7.60 mmol, 1.69 g) and DIEA (31.65 mmol, 4.09 g) in DMF (15 mL) was added HATU (7.6 mmol, 2.89 g). The mixture was stirred at 60° C. for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water (2×), sat. aqueous NaHCO3 (1×), brine (1×), dried and concentrated. The residue was purified by column to give a yellow solid (3.9 g, 95%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09301951B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-ca085ce47aaa4049ba6531228d8a86d3
Source note	uspto-grants-2016_04