155742-64-6

Basic information

• Product Name: N-Methylcarbonyl-2-chloroacetamidrazone
• Synonyms: 2-(2-Chloro-1-iminoethyl)hydrazinecarboxylic Acid Methyl Ester;N-Methylcarbonyl-2-chloroacetamidrazone;Methyl (Z)-2-chloro-1-hydrazino ethylidenecarbamate;N-(methoxycarbonyl)-2-chloroacetamidrazone;(Z)-Methyl 2-(1-aMino-2-chloroethylidene);Methyl 2-(2-chloro-1-iMinoethyl)hydrazinecarboxylate;N-carboMethoxy-2-chloroacetaMidohydrazone;N'-(2-Chloro-1-iMino-ethyl)-hydrazinecarboxylic acid Methyl ester
• CAS NO: 155742-64-6
• Molecular Formula: C₄H₈ClN₃O₂
• Molecular Weight: 165.58
• Product Categories: Chemical Amines;Aliphatics;Amines
• Mol File: 155742-64-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.43
• Refractive Index: 1.531
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly)
• PKA: 7.62±0.43(Predicted)
• CAS DataBase Reference: N-Methylcarbonyl-2-chloroacetamidrazone(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylcarbonyl-2-chloroacetamidrazone(155742-64-6)
• EPA Substance Registry System: N-Methylcarbonyl-2-chloroacetamidrazone(155742-64-6)

Safety Data

• Hazardous Substances Data: 155742-64-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

N-Methylcarbonyl-2-chloroacetamidrazone is useful for preparing the intermediate of Fosaprepitant.

InChI:InChI=1/C4H8ClN3O2/c1-10-4(9)8-7-3(6)2-5/h2H2,1H3,(H2,6,7)(H,8,9)

Upstream product

• 6294-89-9 hydrazinecarboxylic acid methyl ester 
• 107-14-2 chloroacetonitrile 

Downstream Products

• 219821-37-1 2-[2-[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]-1-iminoethyl]hydrazinecarboxylic acid methyl ester 
• 219821-37-1 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(S)-4-fluorophenyl-4-2-(N-methylcarboxyactamidrazono)morpholine 
• 586397-31-1 methyl (2S,3S)-N'-(2-(3-(3,5-bis(trifluoromethyl)benzyloxymethyl)-4-methyl-5-oxo-2-phenylpiperazin-1-yl)-1-iminoethyl)hydrazinocarboxylate 
• 586397-27-5 methyl (5S,6S)-N'-(6-(3,5-bis(trifluoromethyl)benzyloxymethyl)-2-oxo-5-phenylpiperazin-4-yl-1-iminoethyl)hydrazinocarboxylate 
• 869724-05-0 5-[4S-(3,5-bistrifluoromethylbenzyloxy)-3R-2-tolylpiperidine-1-methyl]-2,4-dihydro-[1,2,4]triazol-3-one 

Relevant articles and documents

Structure-activity relationships and CoMFA of N-3 substituted phenoxypropyl piperidine benzimidazol-2-one analogues as NOP receptor agonists with analgesic properties

The N-3 position of a series of 3-phenoxypropyl piperidine benzimidazol-2-one analogues was optimised using the predictive power of a CoMFA model. The model was used to prioritise compounds for synthesis culminating in the triazole (+)-24. (+)-24 was found to be a high affinity, potent NOP agonist and demonstrated both antinociceptive and antiallodynic effects when administered iv to rodents.

N-heteroaryl-2-phenyl-3-(benzyloxy)piperidines: A novel class of potent orally active human NK1 antagonists

The preparation of a series of N-heteroarylpiperidine ether-based human NK1 antagonists is described. Two of the compounds (3-[{(2S,3S)-3-(((3,5- bis(trifluoromethyl)phenyl)methyl)oxy)-2-phenylpiperidino}methyl ]-1,2,4- triazole (11) and 5-[{(2S,3S)-3-(((3,5- bis(trifluoromethyl)phenyl)methyl)oxy)-2-phenylpiperidino}methyl ]-3-oxo- 1,2,4-triazolone (12)), in particular, are orally bioavailable and exhibited significant improvements in potency, both in vitro and in vivo, over the lead (carboxamidomethyl)piperidine ether 1. Rat liver microsome studies on a selected number of compounds from this series show the triazolone heterocycle to be considerably more stable than the others. Furthermore, both 11 and 12 have been profiled in a number of assays that may be predictive of the clinical utility of substance P antagonists.