18637-00-8

Basic information

• Product Name: 2-Ethoxybenzamidine hydrochloride
• Synonyms: 2-ETHOXY-BENZAMIDINE HCL;2-ETHOXYBENZAMIDINE HYDROCHLORIDE;2-Ethoxybenzenecarboximidamide.HCl;Ethoxyamidin;Ethoxy Benzamidine Hydrochloride;2-EthoxybenziMidaMide hydrochloride;Vardenafil IMpurity (2-Ethoxy BenzaMidine Hydrochloride);Vardenafil impurity E
• CAS NO: 18637-00-8
• Molecular Formula: C₉H₁₂N₂O*ClH
• Molecular Weight: 200.67
• EINECS: 242-575-2
• Product Categories: Miscellaneous;pharmacetical;Erectile Dysfunction
• Mol File: 18637-00-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 192oC at 760 mmHg
• Flash Point: 66.7oC
• Appearance: /
• Density: 2.209g/cm3
• Vapor Pressure: 0.5mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2-Ethoxybenzamidine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethoxybenzamidine hydrochloride(18637-00-8)
• EPA Substance Registry System: 2-Ethoxybenzamidine hydrochloride(18637-00-8)

Safety Data

• Hazardous Substances Data: 18637-00-8(Hazardous Substances Data)

Usage

Uses

2-Ethoxybenzamidine hydrochloride is an impurity of Vardenafil (diHCl salt: V098001), a phosphodiesterase type 5 inhibitor that is used to treat men of varying aetiology with erectile dysfunction.

InChI:InChI=1/C3H3Br2ClO/c4-1-2(5)3(6)7/h2H,1H2

Upstream product

• 6609-57-0 2-ethoxybenzonitrile 
• 75-24-1 trimethylaluminum 
• 421-20-5 Methyl fluorosulfonate 
• 64633-71-2 ethyl 2-ethoxybenzimidate fluorosulfonate 
• 938-73-8 2-ethoxybenzamide 

Downstream Products

• 63874-50-0 2-(2-ethoxy-phenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 1255919-01-7 2-[2-ethoxy-5-(4-ethylpiperazine-1-sulfonyl)phenyl]-5-methyl-7-phenyl-3H-imidazo[5,1-f] [1,2,4]triazin-4-one 
• 1569269-00-6 3,5-bis(2-ethoxyphenyl)-4H-1,2,4-triazole 
• 224789-20-2 2-(2-Ethoxyphenyl)-5,7-dimethyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one 
• 224789-25-7 4-ethoxy-3-(5,7-dimethyl-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl)-benzenelsulfonic acid chloride 
• 63874-78-2 Potassium 1,6-dihydro-6-oxo-2-(2-ethoxyphenyl)pyrimidine-5-carboxylate 
• 63874-64-6 1,6-dihydro-6-oxo-2-(2-ethoxyphenyl)-pyrimidine-5-carboxylic acid 
• 63874-75-9 2-(5-dimethylamino-2-ethoxy-phenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid 
• 63874-61-3 2-(5-amino-2-ethoxy-phenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 63874-60-2 2-(2-ethoxy-5-nitro-phenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 927690-90-2 N-{1-[3-(2-ethoxyphenyl)-5-oxo-4,5-dihydro-[1,2,4]triazin-6-yl]ethyl}butyroamide 
• 224789-24-6 2-(2-Ethoxyphenyl)-5-ethyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one 
• 346605-61-6 N-[6-Amino-2-(2-ethoxyphenyl)-4-oxo-5-propyl-4,5-dihydro-pyrimidin-5-yl]-acetamide 
• 224789-21-3 2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one 

Relevant articles and documents

Alternative method for the synthesis of imidazo[5,1-f][1,2,4]triazin-4(3H)- one - A substrate for the preparation of phosphodiesterase (5) inhibitors

Imidazo[5,1-f][1,2,4]triazin-4(3H)-ones, as isosteres of purine, are of interest for pharmaceutical research as potential substrates for the synthesis of cGMP-PDE5 inhibitors. We present a novel, alternative method for the synthesis of imidazotriazinones, that differs from the previously reported ones with respect to the method of construction of the triazinone ring in the molecule. The key step in our approach is condensation of an appropriate α-keto-ester with amidrazones, leading to the triazinone heterocycle. Several different substituted imidazolotriazinones have been synthesized in this manner.

Novel imidazotriazinones and the use thereof

Novel imidazotrizinones of general formula (I), a method for the production and the pharmaceutical use thereof are disclosed.

2-Phenyl-substituited Imidazotriazinones as Phoshodiesterase Inhibitors

2-(Sulfamoyl-substituted phenyl)-3H-imidazo (5,1-f) (1,2,4) triazin-4-ones (I) are new. Imidazotriazinones of formula (I) and their salts, N-oxides and isomeric forms are new: R1 = H or 1-4C alkyl; R2 = 1-4C straight chain alkyl; R3, R4 = H, 2-8C alkenyl, 1-8C alkoxy or 1-10C alkyl (optionally interrupted by O and/or substituted by a very wide range of specific groups); or R3 or R4 = NR20R21, adamantyl, 2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl, sulfolanyl, hydroxy-sulfolanyl, 2-oxo-tetrahydrofuran-3-yl; or 3-8C cycloalkyl, 6-10C aryl or 5-7 membered heterocycle, all optionally substituted by specific groups; or NR3R4 = (a) optionally benzo-fused, saturated, partially unsaturated or unsaturated 5-7 membered heterocycle, optionally containing 1-3 of S, N, O and NR37 and optionally substituted by a very wide range of specific groups; or (b) a group of formula (i)-(iv); R20,R21 = H or 1-6C alkyl; R37 = H, OH, CHO, CF3, up to 4C acyl, up to 4C alkoxycarbonyl, 1-4C alkoxy, 1-6C alkyl (optionally substituted by specific groups) or -(CO)iE; i = 0 or 1; E = 3-7C cycloalkyl or benzyl; 6-10C aryl or 5- or 6-membered heteroaryl, both optionally substituted by specific groups ; or 5-methyl-1-oxo-2,1,3-oxadiazol-4-yl, N-methylpiperazino or morpholino; R5,R6 = H, 1-6C alkyl, OH or 1-6C alkoxy. The full definitions are given in the DEFINITIONS (Full Definitions) field. An Independent claim is included for the preparation of (I).