52583-90-1

Basic information

• Product Name: 2-(cyclopropylamino)nicotinonitrile
• Synonyms: 2-(cyclopropylamino)nicotinonitrile;2-(Cyclopropylamino)-3-cyanopyridine;2-(Cyclopropylamino)-3-pyridinecarbonitrile
• CAS NO: 52583-90-1
• Molecular Formula: C₉H₉N₃
• Molecular Weight: 159.18786
• Mol File: 52583-90-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 334.4±27.0 °C(Predicted)
• Appearance: /
• Density: 1.20
• Storage Temp.: 2-8°C
• PKA: 3.33±0.10(Predicted)
• CAS DataBase Reference: 2-(cyclopropylamino)nicotinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(cyclopropylamino)nicotinonitrile(52583-90-1)
• EPA Substance Registry System: 2-(cyclopropylamino)nicotinonitrile(52583-90-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 52583-90-1(Hazardous Substances Data)

Usage

General Description

2-(cyclopropylamino)nicotinonitrile is a chemical compound with the formula C10H10N4. It is a derivative of the vitamin niacin (nicotinic acid) and contains a cyclopropylamino group. 2-(cyclopropylamino)nicotinonitrile is used in the field of medicinal chemistry as a building block for the synthesis of pharmaceutical compounds. Its unique chemical structure makes it a valuable intermediate in the production of various drugs and biologically active molecules. Research on 2-(cyclopropylamino)nicotinonitrile continues to explore its potential applications in drug discovery and development.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.