Diisopropylethylamine → N-(4-Chloro-3-(N-cyclopropylsulfamoyl)benzyl)-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide

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	4'-Methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid	HCID 58187975	—
Reactant	5-(aminomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide	HCID 65769771	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(4-Chloro-3-(N-cyclopropylsulfamoyl)benzyl)-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide	HCID 58188053	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

To a solution of 4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid (60 mg, 0.19 mmol) in N,N-dimethylformamide (1.0 mL) were added 5-(aminomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide (80 mg, 0.31 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (150 mg, 0.39 mmol) and N,N-diisopropylethylamine (150 μL, 0.86 mmol). The reaction mixture was stirred for 16 hours at 50° C. The reaction mixture was purified by preparative HPLC to afford a light colour solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946439B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-8a85e301894b44ecab3d3af359c2691d
Source note	uspto-grants-2015_02