243145-00-8

Basic information

• Product Name: Vildagliptin Impurity 19
• Synonyms: Vildagliptin Impurity 19;1-Amino-3-nitroadamantane;3-Nitro-adamantan-1-ylamine
• CAS NO: 243145-00-8
• Molecular Formula: C₁₀H₁₆N₂O₂
• Molecular Weight: 196.24624
• Mol File: 243145-00-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 305.9±21.0 °C(Predicted)
• Appearance: /
• Density: 1.25±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.86±0.20(Predicted)
• CAS DataBase Reference: Vildagliptin Impurity 19(CAS DataBase Reference)
• NIST Chemistry Reference: Vildagliptin Impurity 19(243145-00-8)
• EPA Substance Registry System: Vildagliptin Impurity 19(243145-00-8)

Safety Data

• Hazardous Substances Data: 243145-00-8(Hazardous Substances Data)

Usage

Uses

1-Amino-3-nitroadamantane has potential application in co-catalyst for transition metal reactions and maybe a useful intermediate for the synthesis of?Vildagliptin (V305000), an?antidiabetic drug that inhibits dipeptidyl peptidase 4 (DPP-4). Vildagliptin exhibits antioxidant properties and may be an apoptotic compound against pancreatic cancer cells.

Upstream product

• 665-66-7 amantadine hydrochloride 
• 55100-59-9 1,3-dinitroadamantane 
• 7440-02-0 nickel 

Downstream Products

• 702-82-9 3-aminoadamantan-1-ol 

Relevant articles and documents

Method for preparing 3- amino -1- adamantane alcohol

The invention discloses a preparation method of 3-amino-1-adamantanol, which comprises following steps: (1) adding amantadine or a salt thereof to sulfuric acid at 10-30 DEG C and adding dropwisely a mixed acid to perform a nitration reaction to obtain a reaction liquid; (2) adding the reaction liquid to water and mixing the reaction liquid with water to obtain a mixed solution; (3) performing a hydroxylation reaction under the effect of an alkaline to obtain the 3-amino-1-adamantanol . The preparation method employs the raw material being easy to obtain, is simple in operations, is environmental-protective, is low in cost, is high in yield which is generally higher than 80%, maximally 90.1%, and is more suitable for industrial production.

NITRATION OR CARBOXYLATION CATALYSTS

In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the following formula (1): ???wherein R1and R2represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group and a cycloalkyl group, and R1and R2may bond together to form a double bond, or an aromatic or non-aromatic ring, and Y is an O or OH, and n denotes 1 to 3;, a substrate is allowed to contact with at least one reactant selected from (i) a nitrogen oxide and (ii) a mixture of carbon monoxide and oxygen to be introduced with at least one functional group selected from a nitro group and a carboxyl group. The nitrogen oxide includes, for example, a compound represented by the formula NxOy(e.g., N2O3, NO2). The substrate includes, for example, a compound having a methine carbon atom (e.g., adamantane), a compound having a methyl group or a methylene group at an adjacent moiety of an aromatic ring. According to such reaction, the substrate can be efficiently nitrated or carboxylated even in a mild or moderate condition.