4-Amino-4'-chlorodiphenyl → Ethyl 3-(5-(5-chloro-2-((4'-chloro-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)picolinamido)propanoate

Participants

Role	Name	HCID	Charge
Reactant	4-Amino-4'-chlorodiphenyl	HCID 8675	—
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-(6-((2-Carboxyethyl)carbamoyl)pyridin-3-yl)-4-chlorobenzoic acid	HCID 71059998	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Ethyl 3-(5-(5-chloro-2-((4'-chloro-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)picolinamido)propanoate	HCID 71059949	—

Reaction Conditions

Temperature	45 °C

Reaction Steps

Solid HATU (101 mg, 0.27 mmol) was added to a DMF solution (2 mL) of 2-(6-((2-carboxyethyl)carbamoyl)pyridin-3-yl)-4-chlorobenzoic acid (100 mg, 0.27 mmol), i-Pr2NEt (0.2 mL, 1.1 mmol), and 4′-chloro-[1,1′-biphenyl]-4-amine (57 mg, 0.28 mmol) and the resulting mixture was warmed to 45° C. After 16 h the resulting mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748624B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-9fe7b119e178466f95b980ab066eb113
Source note	uspto-grants-2014_06