149463-65-0

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Pyridinyl)butyl chloride hydrochloride is used as a key intermediate in the synthesis of tirofiban hydrochloride, a potent antiplatelet drug. It plays a crucial role in the development of this medication, which is used to treat patients with acute coronary syndrome and to prevent thrombotic events during angioplasty and stent placement.
As an intermediate in the synthesis of other pharmaceutical compounds, 4-(4-Pyridinyl)butyl chloride hydrochloride can be further modified and functionalized to create a variety of drugs with different therapeutic applications. Its unique structure allows for versatile chemical reactions, making it a valuable building block in the development of new medications.

InChI:InChI=1/C9H12ClN.ClH/c10-6-2-1-3-9-4-7-11-8-5-9;/h4-5,7-8H,1-3,6H2;1H

Upstream product

• 108-89-4 picoline 
• 109-70-6 1.3-chlorobromopropane 

Relevant academic research and scientific papers

A practical synthesis of fibrinogen receptor antagonist MK-383. Selective functionalization of (S)-tyrosine

A practical 4-step synthesis of fibrinogen receptor antagonist MK-383, N-(n-butanesulfonyl)-O-4-(4-piperidinyl)-butyl)-(S)-tyrosine, is accomplished in 48% overall yield from (S)-tyrosine. Highlights include: (1) the dual use of 4-picoline as a masked form of piperidine, and as a nucleophile precursor for a 3-carbon homologation with 3-bromo-1-chloropropane; (2) the use of trimethylsilyl groups for temporary protection of phenolic and carboxylate oxygens of (S)-tyrosine that enable selective N-sulfonylation to be carried out in high yield; (3) the selective phenolic O-alkylation of the tyrosine derivative in high yield with no racemization using aqueous KOH/DMSO; and (4) the selective hydrogenation of the pyridine ring in the presence of the tyrosine ring using Pd/C in acetic acid.

Process for preparing fibrinogen receptor antagonists

The invention is a highly efficient synthesis for making compounds of the formula: STR1 wherein: R1 is a six member saturated or unsaturated heterocyclic ring containing one or two heterocyclic atoms wherein the heteroatoms are N; or NR6, wherein R6 is H or C1-10 alkyl; m is an integer from two to six; and R4 is aryl, C1-10 alkyl, or C4-10 aralkyl.