329347-27-5

Basic information

• Product Name: Butanoic acid, 4-[(4-bromo-2-formylphenyl)propylamino]-
• CAS NO: 329347-27-5
• Molecular Formula: C14H18BrNO3
• Molecular Weight: 328.206
• Mol File: 329347-27-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 4-[(4-bromo-2-formylphenyl)propylamino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 4-[(4-bromo-2-formylphenyl)propylamino]-(329347-27-5)
• EPA Substance Registry System: Butanoic acid, 4-[(4-bromo-2-formylphenyl)propylamino]-(329347-27-5)

Safety Data

• Hazardous Substances Data: 329347-27-5(Hazardous Substances Data)

Upstream product

• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 3470-99-3 1-(3-propyl)-pyrrolidin-2-one 

Downstream Products

• 313738-96-4 7-{4-[2-(butoxy)ethoxy]phenyl}-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid 
• 313740-83-9 7-{4-[2-(butoxy)ethoxy]phenyl}-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 329347-28-6 4-(4-bromo-2-formyl-N-propylanilino)-butyric acid ethyl ester 

Relevant articles and documents

Practical synthesis of an orally active CCR5 antagonist, 7-{4-[2-(Butoxy)-ethoxy]phenyl}-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino] methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide

A practical method of synthesizing 7-{4-[2-(butoxy)ethoxy]-phenyl}-N-(4- {[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}-phenyl)-1-propyl-2, 3-dihydro-1H-1-benzazepine-4-carboxamide (8), an orally active CCR5 antagonist, has been developed. Methyl 7-bromo-1-propyl-2,3-dihydro-1H-1-benzazepine-4- caboxylate (14a) was synthesized in good yield by the esterification of 4-[(4-bromo-2-formylphenyl)(propyl)amino]butanoic acid (13) followed by an intramolecular Claisen type reaction with 28% sodium methoxide in dimethyl carbonate as a solvent in one pot. The Suzuki-Miyaura reaction of 14a and 1-bromo-4-(2-butoxyethoxy)benzene (10) followed by hydrolysis and amidation gave 8. A new inexpensive method without chromatographic purification was established.