637031-93-7

Basic information

• Product Name: 3,3-DIFLUOROCYCLOBUTANAMINE HYDROCHLORIDE
• Synonyms: 3,3-DIFLUOROCYCLOBUTANAMINE HYDROCHLORIDE;3,3-Difluorocyclobutanami...;3,3-difluorocyclobutan-1-aMine hydrochloride;(3,3-Difluorocyclobutyl)aMine Hydrochloride;CyclobutanaMine, 3,3-difluoro-, hydrochloride (1:1);3,3-difluorocyclobutanaMine hcl;3,3-Diflurocyclobutanamine hydrochloride;3,3-Difluorocyclobutaneamine (hydrochloride)
• CAS NO: 637031-93-7
• Molecular Formula: C₄H₇F₂N*ClH
• Molecular Weight: 143.56
• EINECS: 1308068-626-2
• Product Categories: Aliphatics;Amines;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 637031-93-7.mol

Chemical Properties

• Melting Point: 296 °C
• Boiling Point: 83.394°C at 760 mmHg
• Flash Point: -11.021°C
• Appearance: /
• Density: 1.175g/cm³
• Vapor Pressure: 75.54mmHg at 25°C
• Refractive Index: 1.405
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: 3,3-DIFLUOROCYCLOBUTANAMINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-DIFLUOROCYCLOBUTANAMINE HYDROCHLORIDE(637031-93-7)
• EPA Substance Registry System: 3,3-DIFLUOROCYCLOBUTANAMINE HYDROCHLORIDE(637031-93-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 637031-93-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,3-Difluorocyclobutanamine hydrochloride is used as a key intermediate for the preparation of piperazinyl antiviral agents. Its incorporation into these agents aids in the development of medications that can effectively combat viral infections by targeting essential viral enzymes or proteins.
Additionally, 3,3-difluorocyclobutanamine hydrochloride is used as a building block for the synthesis of kinase inhibitors. Kinases are enzymes that play a crucial role in cellular signaling pathways, and their dysregulation is often associated with various diseases, including cancer. By inhibiting these enzymes, kinase inhibitors can potentially halt the progression of diseases and offer therapeutic benefits.

InChI:InChI=1/C4H7F2N.ClH/c5-4(6)1-3(7)2-4;/h3H,1-2,7H2;1H

Upstream product

• 939399-53-8 benzyl (3,3-difluorocyclobutyl)carbamate 
• 86770-82-3 3,3-difluorocyclobutane-1-carboxamide 
• 791061-00-2 3,3-difluorocyclobutyl-1-amine 
• 1029720-19-1 tert-butyl (3,3-difluorocyclobutyl)carbamate 
• 107496-54-8 3,3-difluorocyclobutanecarboxylic acid 

Downstream Products

• 1198160-28-9 2-(3,3-difluorocyclobutyl)-3-oxo-N-(4-(trifluoromethoxy)benzyl)isoindoline-1-carboxamide 
• 1309774-29-5 N-3,3-difluorocyclobutylcarbamic acid 4-nitro-phenyl ester 

Relevant articles and documents

3, 3-difluorocyclobutylamine hydrochloride intermediate, synthetic method thereof and synthetic method of 3, 3-difluorocyclobutylamine hydrochloride

The invention relates to a 3, 3-difluorocyclobutylamine hydrochloride intermediate, a synthetic method thereof and a synthetic method of 3, 3-difluorocyclobutylamine hydrochloride. The method comprises the following steps: generating a methyl ester compound from 3-oxo cyclobutanecarboxylic acid under acid catalysis, fluorinating the methyl ester compound to obtain a fluoride, and reacting with hydroxylamine to generate the 3, 3-difluorocyclobutylamine hydrochloride intermediate, subjecting the 3, 3-difluorocyclobutylamine hydrochloride intermediate torearrangement reaction under the action ofsulfonyl chloride and alkali without purification and separation to obtain 3, 3-difluorocyclobutylamine, and finally salifying 3, 3-difluorocyclobutylamine and hydrochloric acid to generate 3, 3-difluorocyclobutylamine hydrochloride. The synthetic method of the 3, 3-difluorocyclobutylamine hydrochloride does not need to use azide, is mild in reaction condition, safe and environment-friendly, is simple in process route, remarkably shortens the production period, has advantages in productivity, and is simple and easily available in raw materials, low in cost and suitable for industrial mass production.

Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents

The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C-N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.

Preparation method of ivosidenib intermediate 3,3-difluorocyclobutanamine hydrochloride

The invention belongs to the technical field of medicine, and specifically relates to a preparation method of 3,3-difluorocyclobutanamine hydrochloride (I). The preparation method comprises the following steps: amidating a compound II, thus obtaining a compound III; reacting with a fluorinated reagent, thus obtaining a compound IV; then carrying out Hofman degradation reaction, thus obtaining a compound V; finally salifying, thus obtaining the 3,3-difluorocyclobutanamine hydrochloride (I). Compared with the prior art, the technical route is simple, the steps are shorter, the cost is low, the reaction condition is gentle, reagents which are toxic and are high in danger coefficient are prevented from being used, the preparation method is green and environmentally friendly, and good application value is obtained.

Multigram Synthesis of C 4/C5 3,3-Difluorocyclobutyl-Substituted Building Blocks

An approach for the multigram synthesis of 3,3-difluorocyclobutyl-substituted building blocks (including carboxylic acid, amines, alcohols, azide, trifluoroborate ketone) is described. It is shown that, in most cases, ethyl 3,3-difluorocyclobutanecarboxylate is a convenient common synthetic intermediate to obtain the target derivatives. For preparation of 3,3-difluorocyclobutanol or -cyclobutanone, an alternative pathway via reaction of dichloroketene and tert -butyl or benzyl vinyl ether should be applied.

Lead Optimization toward Proof-of-Concept Tools for Huntington's Disease within a 4-(1 H -Pyrazol-4-yl)pyrimidine Class of Pan-JNK Inhibitors

Through medicinal chemistry lead optimization studies focused on calculated properties and guided by X-ray crystallography and computational modeling, potent pan-JNK inhibitors were identified that showed submicromolar activity in a cellular assay. Using in vitro ADME profiling data, 9t was identified as possessing favorable permeability and a low potential for efflux, but it was rapidly cleared in liver microsomal incubations. In a mouse pharmacokinetics study, compound 9t was brain-penetrant after oral dosing, but exposure was limited by high plasma clearance. Brain exposure at a level expected to support modulation of a pharmacodynamic marker in mouse was achieved when the compound was coadministered with the pan-cytochrome P450 inhibitor 1-aminobenzotriazole. (Chemical Presented)

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

THERAPEUTICALLY ACTIVE COMPOUNDS AND USE THEREOF

Provided are therapeutically active compounds and the use in manufacture of medicaments for treating a cancer characterized by the presence of a mutant allele of IDH1.

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

Discovery of novel HCV inhibitors: Synthesis and biological activity of 6-(indol-2-yl)pyridine-3-sulfonamides targeting hepatitis C virus NS4B

A novel series of 6-(indol-2-yl)pyridine-3-sulfonamides was prepared and evaluated for their ability to inhibit HCV RNA replication in the HCV replicon cell culture assay. Preliminary optimization of this series furnished compounds with low nanomolar potency against the HCV genotype 1b replicon. Among these, compound 8c has identified as a potent HCV replicon inhibitor (EC50 = 4 nM) with a selectivity index with respect to cellular GAPDH of more than 2500. Further, compound 8c had a good pharmacokinetic profile in rats with an IV half-life of 6 h and oral bioavailability (F) of 62%. Selection of HCV replicon resistance identified an amino acid substitution in HCV NS4B that confers resistance to these compounds. These compounds hold promise as a new chemotype with anti-HCV activity mediated through an underexploited viral target.