5H-Dibenzo[b,f]azepine-5-(~13~C,~15~N)carboxamide

カタログ番号: B3417935

CAS番号: 1173022-00-8

分子量: 236.27 g/mol

InChIキー: FFGPTBGBLSHEPO-UHFFFAOYSA-N

注意: 研究専用です。人間または獣医用ではありません。

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概要

1. 説明

8. Synthesis routes and methods I

2. 準備方法

9. Synthesis routes and methods II

3. 化学反応の分析

10. Synthesis routes and methods III

4. 科学的研究の応用

11. Synthesis routes and methods IV

5. 作用機序

12. Synthesis routes and methods V

6. 類似化合物との比較

13. Retrosynthesis analysis

7. 特性

14. 免責事項

説明

5H-Dibenzo[b,f]azepine-5-(~13~C,~15~N)carboxamide: is a tricyclic compound with a seven-membered ring structure.

準備方法

Synthetic Routes and Reaction Conditions:

Starting Material: The synthesis begins with 5H-Dibenzo[b,f]azepine.

Reaction with Cyanate Salt: The compound is reacted with a cyanate salt, such as alkali metal cyanate salts or alkaline-earth metal cyanate salts.

Purification: The resulting product is purified using methods like chromatography.

Industrial Production Methods: The industrial production of 5H-Dibenzo[b,f]azepine-5-(~13~C,~15~N)carboxamide involves large-scale synthesis using similar reaction conditions but optimized for higher yields and purity. The use of automated reactors and continuous flow systems is common to ensure consistent quality and efficiency .

化学反応の分析

Types of Reactions:

Oxidation: The compound can undergo oxidation reactions to form various oxidized derivatives.

Reduction: Reduction reactions can convert it into different reduced forms.

Substitution: It can participate in substitution reactions, where functional groups are replaced with others.

Common Reagents and Conditions:

Oxidation: Common oxidizing agents include potassium permanganate and hydrogen peroxide.

Reduction: Reducing agents like lithium aluminum hydride and sodium borohydride are used.

Substitution: Reagents such as halogens and alkylating agents are employed.

Major Products:

Oxidized Derivatives: These include various carboxylated and hydroxylated forms.

Reduced Forms: These include hydrogenated derivatives.

Substituted Products: These include halogenated and alkylated derivatives.

科学的研究の応用

Chemistry:

作用機序

Mechanism:

Molecular Targets and Pathways:

Targets include carboxyl groups and various enzymes involved in hydrolysis reactions .

類似化合物との比較

10,11-Dihydro-5H-dibenzo[b,f]azepine:

Carbamazepine: A well-known anticonvulsant drug with a similar structure.

Oxcarbazepine: Another anticonvulsant with a similar core structure.

Uniqueness:

The incorporation of isotopes (~13~C, 15N) in 5H-Dibenzo[b,f]azepine-5-(~13~C,~15~N)carboxamide makes it unique for specific research applications, particularly in tracing and studying metabolic pathways .

特性

IUPAC Name	benzo[b][1]benzazepine-11-(15N)carboxamide	Source
Details	Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)/i15+1,16+1	Source
Details	Computed by InChI 1.0.6 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	FFGPTBGBLSHEPO-IIJSWMDNSA-N	Source
Details	Computed by InChI 1.0.6 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	C1=CC=C2C(=C1)C=CC3=CC=CC=C3N2C(=O)N	Source
Details	Computed by OEChem 2.3.0 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Isomeric SMILES	C1=CC=C2C(=C1)C=CC3=CC=CC=C3N2[13C](=O)[15NH2]	Source
Details	Computed by OEChem 2.3.0 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C15H12N2O	Source
Details	Computed by PubChem 2.1 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

DSSTOX Substance ID	DTXSID30678690	Source
Record name	5H-Dibenzo[b,f]azepine-5-(~13~C,~15~N)carboxamide
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID30678690
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	238.25 g/mol	Source
Details	Computed by PubChem 2.1 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

CAS No.	1173022-00-8	Source
Record name	5H-Dibenzo[b,f]azepine-5-(~13~C,~15~N)carboxamide
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID30678690
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Record name	1173022-00-8
Source	European Chemicals Agency (ECHA)
URL	https://echa.europa.eu/information-on-chemicals
Description	The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness.
Explanation	Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.

Synthesis routes and methods I

Procedure details

A suspension of 10 g of iminostilbene in 100 ml toluene was treated with 20.2 g of sodium cyanate and 27.5 g of mandelic acid and was heated to reflux for about 10 hrs. The reaction mixture was cooled to room temperature and charged with sodium hydroxide solution and maintained for 8 hrs. The resulting suspension was filtered, washed with water and dried to give 11 g of carbamazepine.

Name

iminostilbene

Quantity

10 g

Type

reactant

Reaction Step One

Name

toluene

Quantity

100 mL

Type

solvent

Reaction Step One

Name

sodium cyanate

Quantity

20.2 g

Type

reactant

Reaction Step Two

Name

mandelic acid

Quantity

27.5 g

Type

reactant

Reaction Step Two

Name

sodium hydroxide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

carbamazepine

Details

Synthesis routes and methods II

Procedure details

To a suspension of urea (80 g, 1.333 mols) in acetic acid (100 ml), phosphoric acid (8 ml) was added, followed by iminostilbene (20 g, 0.103 mols), under stirring at 25-30° C. The resulting reaction mixture was worked up according to the method of Example 1 to produce carbamazepine, which was identical to the product of Example 1.

Name

urea

Quantity

80 g

Type

reactant

Reaction Step One

Name

acetic acid

Quantity

100 mL

Type

solvent

Reaction Step One

Name

phosphoric acid

Quantity

8 mL

Type

solvent

Reaction Step One

Name

iminostilbene

Quantity

20 g

Type

reactant

Reaction Step Two

Name

carbamazepine

Details

Synthesis routes and methods III

Procedure details

To a suspension of urea hydrochloride (100 g, 1.036 mols) in acetic acid (125 ml), iminostilbene (25 g, 0.129 mols) was added under stirring at 25-30° C. The resulting reaction mixture was worked up according to the method of Example 1 to produce carbamazepine, which was identical to the product of Example 1.

Name

urea hydrochloride

Quantity

100 g

Type

reactant

Reaction Step One

Name

iminostilbene

Quantity

25 g

Type

reactant

Reaction Step One

Name

acetic acid

Quantity

125 mL

Type

solvent

Reaction Step One

Name

carbamazepine

Details

Synthesis routes and methods IV

Procedure details

To a suspension of urea (80 g, 1.333 mols) in acetic acid (100 ml), iminostilbene hydrochloride (20.5 g, 0.089 mols) was added under stirring at 25-30° C. The resulting reaction mixture was worked up according to the method of Example 1 to produce carbamazepine, which was identical to the product of Example 1.

Name

urea

Quantity

80 g

Type

reactant

Reaction Step One

Name

iminostilbene hydrochloride

Quantity

20.5 g

Type

reactant

Reaction Step One

Name

acetic acid

Quantity

100 mL

Type

solvent

Reaction Step One

Name

carbamazepine

Details

Synthesis routes and methods V

Procedure details

30 g iminostilbene are heated to 60° C. in 360 ml acetic acid and 50 ml ethanol, and 20 g 98% sodium cyanate is added within 1.5 hours at this temperature. After a short heating to 80° C., the mixture is further stirred at 60° C., and then cooled to 15° C., sucked off, washed with 20 l acetic acid and dried to yield 29.4 g (80.3% of theoretical) of carbamazepine, having a melting point of 189° C. to 192° C.

Name

iminostilbene

Quantity

30 g

Type

reactant

Reaction Step One

Name

acetic acid

Quantity

360 mL

Type

solvent

Reaction Step One

Name

sodium cyanate

Quantity

20 g

Type

reactant

Reaction Step Two

Name

ethanol

Quantity

50 mL

Type

solvent

Reaction Step Two

Name

carbamazepine

Yield

80.3%

Details

Retrosynthesis Analysis

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Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6