Diisopropylethylamine → Tert-butyl 16-(3-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzyl carbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)-4,7,10,13-tetraoxahexadecan-1-oate

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	HCID 66586798	HCID 66586798	—
Reactant	3-(3-(2-(2-(2-(3-Tert-butoxy-3-oxopropoxy)ethoxy)ethoxy)ethoxy)propyl)benzoic acid	HCID 66586891	—
Catalyst	HCID 66586798	HCID 66586798	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Tert-butyl 16-(3-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzyl carbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)-4,7,10,13-tetraoxahexadecan-1-oate	HCID 67512796	77.3%

Reaction Steps

To a solution of 2-(2-amino-5-(diethylamino)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide (1.77 g, 4.0 mmol), 3-(2,2-dimethyl-4-oxo-3,7,10,13,16-pentaoxanonadecan-19-yl)benzoic acid (1.70 g, 3.86 mmol) and DIPEA (1.47 g, 11.4 mmol) in DMF (20 ml) was added HATU (1.56 g, 4.10 mmol). The reaction mixture was stirred for 30 minutes, at which time additional 2-(2-amino-5-(diethylamino)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide (0.06 g, 0.14 mmol) was added. After stirring an additional 25 minutes, the reaction mixture was concentrated under vacuum. The residue was dissolved in DCM (200 mL), washed with water (4×50 mL), dried (Na2SO4) and concentrated to dryness. Purification by flash chromatography on silica gel (50% to 100% EtOAc in hexanes) gave the title compound (2.58 g) as an oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08916569B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-5b58917933c147aaa628d7bca76bc9b0
Source note	uspto-grants-2014_12