52583-90-1

Usage

Uses

Used in Medicinal Chemistry:
2-(Cyclopropylamino)nicotinonitrile is used as a building block for the synthesis of pharmaceutical compounds, contributing to the development of various drugs and biologically active molecules. Its distinctive structure makes it a key component in the creation of new therapeutic agents.
Used in Drug Discovery and Development:
In the pharmaceutical industry, 2-(cyclopropylamino)nicotinonitrile is employed as a research intermediate to explore its potential applications in drug discovery and development. Ongoing research aims to leverage its unique properties to advance the creation of novel therapeutics and enhance existing drug formulations.

Upstream product

• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 765-30-0 Cyclopropylamine 

Downstream Products

• 133627-47-1 N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide 
• 129618-40-2 Nevirapine 
• 639807-18-4 2-(cyclopropylamino)pyridine-3-carboxylic acid 

Relevant academic research and scientific papers

Increasing global access to the high-volume HIV drug nevirapine through process intensification

Access to affordable medications continues to be one of the most pressing issues for the treatment of disease in developing countries. For many drugs, synthesis of the active pharmaceutical ingredient (API) represents the most financially important and technically demanding element of pharmaceutical operations. Furthermore, the environmental impact of API processing has been well documented and is an area of continuing interest in green chemical operations. To improve drug access and affordability, we have developed a series of core principles that can be applied to a specific API, yielding dramatic improvements in chemical efficiency. We applied these principles to nevirapine, the first non-nucleoside reverse transcriptase inhibitor used in the treatment of HIV. The resulting ultra-efficient (91% isolated yield) and highly-consolidated (4 unit operations) route has been successfully developed and implemented through partnerships with philanthropic entities, increasing access to this essential medication. We anticipate an even broader global health impact when applying this model to other active ingredients.

LOWCOST, HIGH YIELD SYNTHESIS OF NEVIRAPINE

Improved methods of producing the HIV drug substance, nevirapine are provided. The methods employ a cost effective and high yield synthetic methods for preparing the nevirapine building block 2-chloro-3-amino-4-picoline (CAPIC) and 2-cyclopropyl amino nicotinate (Me-CAN), and improvements in other steps of nevirapine synthesis.

Method for making nevirapine

A process for making nevirapine, comprising the following steps: (a) reacting a 2-halo-3-pyridinecarbonitrile of the formula ?wherein X is a fluorine, chlorine, bromine or iodine atom, preferably chlorine or bromine, with cyclopropylamine, to yield 2-(cyclopropylamino)-3-pyridinecarbonitrile; (b) hydrolyzing the 2-(cyclopropylamino)-3-pyridinecarbonitrile to yield 2-(cyclopropylamino)-3-pyridine carboxylic acid; (c) isolating the 2-(cyclopropylamino)-3-pyridine carboxylic acid from the reaction medium; (e) treating the 2-(cyclopropylamino)-3-pyridine carboxylic acid with a chlorinating agent, to yield 2-(cyclopropylamino)-3-pyridinecarbonyl chloride; (f) reacting the 2-(cyclopropylamino)-3-pyridine carbonyl chloride with a 2-halo-4-methyl-3-pyridinamine of the formula ?wherein X is a fluorine, chlorine, bromine or iodine atom, preferably chlorine or bromine, to produce an N-(2-halo-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide; and (g) cyclizing the N-(2-halo-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide by treatment with a strong base, to yield nevirapine.