Diisopropylethylamine → HCID 66586889, 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 66586895	HCID 66586895	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 66586889	HCID 66586889	98.1%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a mixture of (S)-2-(2-amino-5-(diethylamino)phenyl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isonicotinamide (7.1 mmol, 2.94 g), 3-(tert-butoxycarbonyl)benzoic acid (8.52 mmol, 1.89 g) and DIEA (35.5 mmol, 4.59 g) in DMF (16 mL) was added HATU (8.52 mmol, 3.24 g). The mixture was stirred at 60° C. for 1 h. The reaction mixture was diluted with ethyl acetate, washed with water (2×), brine (1×), dried and concentrated. The residue was purified by column to give a yellow solid (4.31 g, 98%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09301951B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-cc0eb1c795924efd89d304fb6db0973d
Source note	uspto-grants-2016_04