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

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

Uses

Used in Pharmaceutical Industry:
N-Methylcarbonyl-2-chloroacetamidrazone is used as an intermediate for the preparation of Fosaprepitant, a drug that belongs to the class of neurokinin 1 (NK1) receptor antagonists. It is primarily used for the prevention of nausea and vomiting associated with chemotherapy and radiotherapy treatments. Its role as an intermediate in the synthesis of Fosaprepitant makes it a vital component in the development of antiemetic medications.
The compound's white solid form and its specific reactivity in chemical reactions make it suitable for use in the pharmaceutical industry, where it contributes to the creation of medications that help alleviate the side effects of cancer treatments.

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

• 869724-05-0 5-[4S-(3,5-bistrifluoromethylbenzyloxy)-3R-2-tolylpiperidine-1-methyl]-2,4-dihydro-[1,2,4]triazol-3-one 
• 586397-27-5 methyl (5S,6S)-N'-(6-(3,5-bis(trifluoromethyl)benzyloxymethyl)-2-oxo-5-phenylpiperazin-4-yl-1-iminoethyl)hydrazinocarboxylate 
• 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 
• 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 

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.

ARYL SUBSTITUTED IMIDAZO [4,5-C] PYRIDINE COMPOUNDS AS C3A RECEPTOR ANTAGONISTS

Aryl substituted imidazo[4,5-c] pyridine compounds of formula (I) or pharmaceutically acceptable salt thereof are provided. These compounds are useful in pharmaceutical compositions as C3a antagonists for treating a variety of medical conditions associated with the Complement cascade.

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.