124932-43-0

Basic information

• Product Name: (R)-3-Amino-Hexahydro-1H-Azepin
• Synonyms: (R)-3-Aminohexahydroazepine;(R)-3-AMINO -HEXAHYDRO-1A-AZEPINE;(R)-Azepan-3-aMine;(3R)-azepan-3-aMine;Besifloxacin Impurity G;1H-Azepin-3-amine, hexahydro-, (3R)-;R-3-Aminohomopiperidine;(R)-Hexahydro-1H-azepin-3-amine
• CAS NO: 124932-43-0
• Molecular Formula: C6H14N2
• Molecular Weight: 114.18876
• EINECS: 1308068-626-2
• Mol File: 124932-43-0.mol

Chemical Properties

• Boiling Point: 180.9℃
• Flash Point: 69.6℃
• Appearance: /
• Density: 0.893
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 10.66±0.40(Predicted)
• CAS DataBase Reference: (R)-3-Amino-Hexahydro-1H-Azepin(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-Amino-Hexahydro-1H-Azepin(124932-43-0)
• EPA Substance Registry System: (R)-3-Amino-Hexahydro-1H-Azepin(124932-43-0)

Safety Data

• Hazardous Substances Data: 124932-43-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-Amino-Hexahydro-1H-Azepin is used as a key intermediate for the synthesis of ureido thiophene carboxamides, which are known as checkpoint kinase inhibitors. These inhibitors play a significant role in the development of cancer therapeutics, as they target specific proteins involved in cell cycle regulation and DNA damage response, thereby preventing the uncontrolled proliferation of cancer cells.
Additionally, (R)-3-Amino-Hexahydro-1H-Azepin is identified as an impurity in Besifloxacin (B319000, HCl salt), a fluoroquinolone antibiotic. Besifloxacin is used to treat bacterial infections, particularly those caused by gram-negative and gram-positive bacteria. The presence of (R)-3-Amino-Hexahydro-1H-Azepin as an impurity highlights the importance of its synthesis and purification for the production of high-quality antibiotics.

Upstream product

• 171257-01-5 ε-caprolactam 
• 870842-23-2 3-oxoazepane-1-carboxylic acid tert-butyl ester 
• 146407-32-1 1-benzylazepan-3-one 
• 643045-39-0 C₈H₁₆N₂O 
• 2323-81-1 ethyl 5-chloropentanoate 
• 21568-87-6 2-aminocaprolactam 
• 26081-03-8 (S)-3-aminocaprolactam hydrochloride 
• 454451-26-4 3-tert-butyloxycarbonylamino-1H-azacycloheptane 
• 1354351-56-6 (R)-3-tert-butyloxycarbonylamino-1H-azacycloheptane 

Downstream Products

• 609789-17-5 1-tert-butoxycarbonyl-3-amino-hexahydroazepine 

Relevant articles and documents

3 - Substituted amino - hexahydro - 1 H - nitrogen heterocyclic heptane splitting method

The invention discloses a method for resolving racemic 3-t-butyloxycarboryl amino-hexahydro-1H-azacycloheptane, 3-trityl amino-hexahydro-1H-azacycloheptane, or 3-amino-hexahydro-1H-azacycloheptane by taking L-tartaric acid or a derivative of L-tartaric acid, L-mandelic acid or a derivative of L-mandelic acid as a resolving agent, and discloses a method for preparing (R)-3-amino-hexahydro-1H-azacycloheptane by using (R)-3-t-butyloxycarboryl amino-hexahydro-1H-azacycloheptane or (R)-3-trityl amino-hexahydro-1H-azacycloheptane obtained with the resolution method. The methods are simple and practical, and are suitable for large-scale industrial production.

Method for preparing beixifloxacin intermediate compound

The invention provides a method for preparing a beixifloxacin intermediate compound VI. The method comprises the steps of: reacting a compound of a formula III with an upper protective group, an aminotransferase catalying and a deprotecting group to obtain a compound shown in a formula VI. The method can be used for preparing the beixifloxacin intermediate compound VI rapidly and effectively. Rawmaterials are simple and easy to obtain, the reaction is simple and easy to operate, harsh reaction conditions are not required, a production period is short, yield of a target product is high, separation and purification of the target product are simple, optical purity is high, the method is easy to achieve mass production.

Novel chiral derivatizing agents for 1H NMR determination of enantiomeric purities of carboxylic acids

(S)-4-(3-Aminopyrrolidin-1-yl)coumarin (1), (S)-4-(3-aminopiperidin-1-yl)coumarin (4), and (S)-4-(3-aminoazepan-1-yl)coumarin (7), prepared from 4-chlorocoumarin and (S)-pyrrolidin-3-amine, (S)-piperidin-3-amine, and (S)-azepan-3-amine, respectively, were proven to be versatile and reliable 1H NMR optical purity determination agents for chiral carboxylic acids.

Method for preparing R-3-amino-hexahydroazepine

The invention discloses a method for preparing R-3-amino-hexahydroazepine. The method comprises the steps: (1) synthesizing R-alpha-aminocaprolactam; and (2) synthesizing R-3-amino-hexahydroazepine. Compared with the prior art, the method for preparing R-3-amino-hexahydroazepine, disclosed by the invention, has the advantages that the raw materials are cheaper, the steps are less, the yield is higher, and the aftertreatment is simple.

COMPOUNDS AND COMPOSITIONS FOR MODULATING EGFR ACTIVITY

The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating EGFR activity, as well as methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated EGFR activity.

Tricyclic pharmacophore-based molecules as novel integrin αvβ3 antagonists. Part III: Synthesis of potent antagonists with αvβ3/α IIbβ3 dual activity and improved water solubility

In order to optimize our novel integrin αvβ 3/αIIbβ3 dual antagonists, spatial screening at the N-terminus was performed. The αvβ 3 antagonistic activity varied depending on the space that was occupied by the N-terminus, but high potency against αIIbβ 3 was well maintained. The (3S)-aminopiperidine analogue had the strongest activity against αvβ3, and the S isomer at piperidine was more potent than the R isomer. Compounds selected on the basis of SAR analysis of a novel lead compound showed acceptable early absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiles and sufficient water solubility for use as infusion drugs. Docking studies with the αvβ3 receptor were performed to confirm the SAR findings.

SUCCINATE SALTS OF HETEROCYCLIC DPP-IV INHIBITORS

The present invention relates to therapeutically active and selective hemisuccinate salts of inhibitors of the enzyme DPP-IV of formula (I), pharmaceutical compositions comprising the salts and the use of such salts for and the manufacture of medicaments for treating diseases that are associated with proteins that are subject to inactivation by DPP-IV, such as type 2 diabetes and obesity.

HETEROCYCLIC COMPOUNDS THAT ARE INHIBITORS OF THE ENZYME DPP-IV

The present invention relates to therapeutically active and selective inhibitors of the enzyme DPP-IV of formula I, pharmaceutical compositions comprising the compounds and the use of such compounds for and the manufacture of medicaments for treating diseases that are associated with proteins that are subject to inactivation by DPP-IV, such as type 2 diabetes and obesity.

Cyclic amine derivatives and their use as drugs

A compound represented by the general formula (I), a pharmaceutically acceptable acid addition salt thereof or a pharmaceutically acceptable C1-C6alkyl addition salt thereof, and their medical applications. These compounds inhibit the action of chemokines such as MIP-1α and/or MCP-1 on target cells, and are useful as therapeutic and/or preventative drugs in diseases, such as atheroclerosis, rheumatoid arthritis, and the like where blood monocytes and lymphocytes infiltrate into tissues.

REMEDIES OR PREVENTIVES FOR DISEASES IN ASSOCIATION WITH CHEMOKINES

This invention provides remedies or prophylactics for diseases in association with chemokines such as MIP-1 α and/or MCP-1. Namely, remedies or prophylactics for diseases in association with the chemokines such as rheumatoid arthritis or nephritis contain