330784-50-4

Basic information

• Product Name: 5-Pyrimidinecarboxamide, 2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-4-[[(4-methoxyphenyl)methyl]amino]-N-(2-pyrimidinylmethyl)-
• Synonyms: 5-Pyrimidinecarboxamide, 2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-4-[[(4-methoxyphenyl)methyl]amino]-N-(2-pyrimidinylmethyl)-;(R)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-4-((4-methoxybenzyl)amino)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide;Avanafil Impurity 28
• CAS NO: 330784-50-4
• Molecular Formula: C₂₃H₂₇N₇O₃
• Molecular Weight: 449.50558
• EINECS: -0
• Mol File: 330784-50-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Pyrimidinecarboxamide, 2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-4-[[(4-methoxyphenyl)methyl]amino]-N-(2-pyrimidinylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Pyrimidinecarboxamide, 2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-4-[[(4-methoxyphenyl)methyl]amino]-N-(2-pyrimidinylmethyl)-(330784-50-4)
• EPA Substance Registry System: 5-Pyrimidinecarboxamide, 2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-4-[[(4-methoxyphenyl)methyl]amino]-N-(2-pyrimidinylmethyl)-(330784-50-4)

Safety Data

• Hazardous Substances Data: 330784-50-4(Hazardous Substances Data)

Usage

Uses

3-Deschloro Avanafil is an impurity of avanafil (A794670). Avanafil is a phosphodiesterase (PDE5) inhibitor, used to treat erectile dysfunction.

Upstream product

• 476449-27-1 (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-phenylthio-5-[N-(2-pyrimidylmethyl)carbamoyl]pyrimidine 
• 2393-23-9 4-methoxy-benzylamine 
• 5909-24-0 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester 
• 53554-29-3 ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate 
• 75985-45-4 2-aminomethylpyrimidine 
• 211230-35-2 4-(4-methoxybenzylamino)-2-methanesulfanyl-pyrimidine-5-carboxylic acid ethyl ester 

Relevant articles and documents

Identification, synthesis and characterization of avanafil process impurities and determination by UPLC

Avanafil is a phosphodiesterase type 5 inhibitor which is used to treat erectile dysfunction in men. The process-related impurities of avanafil were investigated, and four kinds of impurities in several laboratory batches with a content of 0.29-1.63% were detected by the newly developed gradient ultra-high performance liquid chromatography (UPLC). Based on the synthesis route and UPLC-MS research, the impurities are inferred as Imp-A, Imp-B, Imp-C and Imp-D. The structures of the impurities were inferred from LC-MS studies and confirmed by synthesis, followed by spectroscopic characterization such as NMR and mass spectrometry. Especially, the synthesis of Imp-D is firstly reported. The drug-related substances can be separated well by efficient and selective ultra-high performance liquid chromatography on a Waters ACQUITY HSS C18 (50 × 2.1 mm, particle size 1.8 μm) column at 35 °C, with the mobile phase consisting of ammonium formate (20 mM) and acetonitrile, and the detection at 239 nm with a DAD detector. The method was validated in terms of specificity, linearity, precision, accuracy and sensitivity, and satisfactory results were obtained. The results indicated this developed UPLC method for avanafil and the proposed synthesis mechanism can be used for quality control purposes as required by regulatory agencies to ensure the safety and efficacy of the product.