382637-68-5

Basic information

• Product Name: 4-(1-Methyl-1H-tetrazol-5-yl)phenylAmine
• Synonyms: 4-(1-Methyl-1H-tetrazol-5-yl)phenylAmine;4-(1-methyl-1H-tetrazol-5-yl)Benzenamine;4-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)aniline
• CAS NO: 382637-68-5
• Molecular Formula: C₈H₉N₅
• Molecular Weight: 175.19
• Mol File: 382637-68-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 392.322 °C at 760 mmHg
• Flash Point: 191.07 °C
• Appearance: /
• Density: 1.4 g/cm³
• CAS DataBase Reference: 4-(1-Methyl-1H-tetrazol-5-yl)phenylAmine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1-Methyl-1H-tetrazol-5-yl)phenylAmine(382637-68-5)
• EPA Substance Registry System: 4-(1-Methyl-1H-tetrazol-5-yl)phenylAmine(382637-68-5)

Safety Data

• Hazardous Substances Data: 382637-68-5(Hazardous Substances Data)

Upstream product

• 20743-51-5 1-methyl-5-(4-nitrophenyl)-1H-tetrazole 
• 122-04-3 4-nitro-benzoyl chloride 
• 2585-23-1 N-methyl-4-nitrobenzamide 
• 62-23-7 4-nitro-benzoic acid 

Downstream Products

• 382637-69-6 [4-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl ester 

Relevant articles and documents

A Convenient One-Pot Synthesis of 1,5-Disubstituted Tetrazoles Containing an Amino or a Carboxy Group

Abstract: A convenient method is proposed for constructing the tetrazole ring by a one-pot reaction of amides with phosphorus oxychloride and sodium azide. A series of 1,5-disubstituted tetrazoles containing an amino or a carboxy group, which present interest as buildings blocks for the synthesis of biologically active substances, were obtained.

Discovery of CC chemokine receptor-3 (CCR3) antagonists with picomolar potency

Starting with our previously described20 class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase I clinical trials.

N-ureidoalkyl-piperidines as modulators of chemokine receptor activity

The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.