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103255-66-9

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  • TIANFU-CHEM - 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-[2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-oxoethyl]-3H-isoindol-1-one

    Cas No: 103255-66-9

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103255-66-9 Usage

Description

2-(7-Chloro-1,8-naphthyridin-2-yl)-3-[2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-oxoethyl]-3H-isoindol-1-one is a complex organic compound characterized by its unique molecular structure. It is composed of a 3H-isoindol-1-one core, with a 7-chloro-1,8-naphthyridin-2-yl group attached at the 2nd position and a 2-oxoethyl group connected to a 1,4-dioxa-8-azaspiro[4.5]decan-8-yl moiety at the 3rd position. 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-[2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-oxoethyl]-3H-isoindol-1-one holds potential for various applications due to its specific structural features and properties.

Uses

Used in Pharmaceutical Industry:
2-(7-Chloro-1,8-naphthyridin-2-yl)-3-[2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-oxoethyl]-3H-isoindol-1-one is used as an active pharmaceutical ingredient (API) for the development of new drugs targeting specific medical conditions. Its unique structure may provide novel mechanisms of action and therapeutic benefits in treating various diseases.
Used in Chemical Research:
In the field of chemical research, this compound can be utilized as a starting material or a scaffold for the synthesis of new molecules with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.
Used in Drug Delivery Systems:
Similar to gallotannin, 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-[2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-oxoethyl]-3H-isoindol-1-one may be employed in the development of drug delivery systems to improve the bioavailability, targeting, and overall efficacy of associated therapeutic agents.
It is important to note that the specific applications and reasons for using this compound may vary depending on the industry and the intended use. Further research and development would be required to fully understand its potential and optimize its application in various fields.

Pharmacokinetics

Pazinaclone is a sedative and anxiolytic drug in the cyclopyrrolone family of drugs. Other cyclopyrrolone drugs include zopiclone and eszopiclone. Pazinaclone has a very similar pharmacological profile to the benzodiazepine family of drugs including sedative and anxiolytic properties, but with less amnestic effects, and at low doses it is a relatively selective anxiolytic, with sedative effects only appearing at higher doses. Pazinaclone produces its sedative and anxiolytic effects by acting as a partial agonist at GABAA benzodiazepine receptors, although pazinaclone is more subtype-selective than most benzodiazepines.

Check Digit Verification of cas no

The CAS Registry Mumber 103255-66-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,3,2,5 and 5 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 103255-66:
(8*1)+(7*0)+(6*3)+(5*2)+(4*5)+(3*5)+(2*6)+(1*6)=89
89 % 10 = 9
So 103255-66-9 is a valid CAS Registry Number.
InChI:InChI=1/C25H23ClN4O4/c26-20-7-5-16-6-8-21(28-23(16)27-20)30-19(17-3-1-2-4-18(17)24(30)32)15-22(31)29-11-9-25(10-12-29)33-13-14-34-25/h1-8,19H,9-15H2

103255-66-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-[2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-oxoethyl]-3H-isoindol-1-one

1.2 Other means of identification

Product number -
Other names 8-[[[2-(7-Chloro-1,8-naphthyridin-2-yl)-2,3-dihydro-3-oxo-1H-isoindol]-1-yl]acetyl]-1,4-dioxa-8-azaspiro[4.5]decane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:103255-66-9 SDS

103255-66-9Synthetic route

2,7-dichloro-1,8-naphthyridine
55243-02-2

2,7-dichloro-1,8-naphthyridine

3-(2-oxo-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)isoindolin-1-one

3-(2-oxo-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)isoindolin-1-one

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one
103255-66-9

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; Schlenk technique; Inert atmosphere;80%
N-(7-chloro-1,8-naphthyridin-2-yl)benzamide
104917-09-1

N-(7-chloro-1,8-naphthyridin-2-yl)benzamide

1-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)propenone
79404-70-9

1-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)propenone

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one
103255-66-9

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In acetonitrile at 80℃; Inert atmosphere; Sealed tube;68%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In acetonitrile at 80℃; for 10h; Schlenk technique; Inert atmosphere;68%
carbon monoxide
201230-82-2

carbon monoxide

2-chloro-7-amino-1,8-naphthyridine
15944-33-9

2-chloro-7-amino-1,8-naphthyridine

8-[(2E)-3-(2-iodophenyl)prop-2-enoyl]-1,4-dioxa-8-azaspiro[4.5]decane

8-[(2E)-3-(2-iodophenyl)prop-2-enoyl]-1,4-dioxa-8-azaspiro[4.5]decane

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one
103255-66-9

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; trifuran-2-yl-phosphane; caesium carbonate In 1,4-dioxane at 110℃; under 760 Torr; Michael addition;64%
1-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)propenone
79404-70-9

1-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)propenone

benzaldehyde
100-52-7

benzaldehyde

2-chloro-7-amino-1,8-naphthyridine
15944-33-9

2-chloro-7-amino-1,8-naphthyridine

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one
103255-66-9

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In acetonitrile at 80℃; Inert atmosphere; Sealed tube;20%
2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxoisoindoline-1-acetic acid
103255-87-4

2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxoisoindoline-1-acetic acid

diethyl cyanophosphonate
2942-58-7

diethyl cyanophosphonate

4,4-ethylenedioxy-piperidine
177-11-7

4,4-ethylenedioxy-piperidine

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one
103255-66-9

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one

Conditions
ConditionsYield
With triethylamine In N-methyl-acetamide; water
methyl 2-(2-acetyl-3-oxoisoindolin-1-yl)acetate

methyl 2-(2-acetyl-3-oxoisoindolin-1-yl)acetate

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one
103255-66-9

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide; water / methanol / 0.5 h / 60 °C / Schlenk technique; Inert atmosphere
2: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Schlenk technique; Inert atmosphere
3: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate; potassium carbonate / 1,4-dioxane / 80 °C / Schlenk technique; Inert atmosphere
View Scheme
(3-oxo-2,3-dihydro-1H-isoindol-1-yl)-acetic acid
3849-22-7

(3-oxo-2,3-dihydro-1H-isoindol-1-yl)-acetic acid

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one
103255-66-9

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Schlenk technique; Inert atmosphere
2: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate; potassium carbonate / 1,4-dioxane / 80 °C / Schlenk technique; Inert atmosphere
View Scheme
2-(2-methoxycarbonylethyl)benzoic acid
33779-03-2

2-(2-methoxycarbonylethyl)benzoic acid

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one
103255-66-9

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Selectfluor; copper(II) nitrate; iron(III)-acetylacetonate / 12 h / 100 °C / Schlenk technique; Inert atmosphere
2: sodium hydroxide; water / methanol / 0.5 h / 60 °C / Schlenk technique; Inert atmosphere
3: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Schlenk technique; Inert atmosphere
4: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate; potassium carbonate / 1,4-dioxane / 80 °C / Schlenk technique; Inert atmosphere
View Scheme
benzoyl chloride
98-88-4

benzoyl chloride

2-chloro-7-amino-1,8-naphthyridine
15944-33-9

2-chloro-7-amino-1,8-naphthyridine

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one
103255-66-9

2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 5.5 h / 0 - 20 °C
2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate / acetonitrile / 80 °C / Inert atmosphere; Sealed tube
View Scheme

103255-66-9Downstream Products

103255-66-9Relevant articles and documents

Synthesis of 3-substituted isoindolin-1-ones via a palladium-catalysed 3-component carbonylation/amination/Michael addition process

Gaj, Xinjie,Grigg, Ronald,Khamnaen, Tossapol,Rajviroongit, Shuleewan,Sridharan, Visuvanathar,Zhang, Lixin,Collard, Simon,Keep, Ann

, p. 7441 - 7444 (2003)

A novel palladium-catalysed three component cascade process is described involving carbonylation of an aryl iodide to generate an acyl palladium species which is intercepted by a primary aliphatic/aromatic amine, amide or sulfonamide followed by intramolecular Michael addition to afford 3-substituted isoindolin-1-ones in good yield.

Preparation method of anti-anxiety drug pagoclone or pazinaclone

-

Paragraph 0034; 0035; 0036; 0037; 0038, (2019/04/09)

The invention discloses a method for catalytically synthesizing an anti-anxiety drug pagoclone or pazinaclone and analogues thereof by utilizing Rh(III). The method comprises the following steps: reacting benzaldehyde and 2-aminopyridine compounds in a solvent in the presence of a rhodium catalyst and acetate, and producing an effective guide group in situ; and reacting the guide group and substituted olefin under rhodium catalysis, and performing after-treatment after the reaction is completed, thereby obtaining a compound having a nitrogen heterocyclic framework. According to the preparationmethod, two independent reactions (amide formation and carbon-hydrogen activation) are catalyzed by using rhodium, and a synthetic strategy of self-assembling high-efficiency guide groups is successfully realized. The reaction is carried out based on simple raw materials, an isoindoxone skeleton having substitution characteristics is synthesized in a simple and mild catalytic system by utilizinga 'one-pot process', the operation is simple and convenient, the reaction conditions are mild, the yield is high, and atom economy is high.

Isoindolinone derivatives, production and use thereof

-

, (2008/06/13)

A compound of the formula STR1 wherein X is hydrogen, halogen or nitro; Ar is phenyl or naphthyridinyl which may optionally be substituted; and either one of Z 1 and Z 2 is hydrogen and the other is lower alkanoyloxy or hydroxy, each of Z 1 and Z 2 is lower alkoxy, or Z 1 and Z 2 combinedly represent hydroxyimino, oxo or a group of the formula: STR2 in which Y is oxygen or sulfur and A is a branched or unbranched lower alkylene chain; and a salt thereof, act on the central nervous system but are weak in adverse effects such as hypnotic and muscle relaxant effects.

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