CAS No.103255-66-9,2-(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 Suppliers

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Basic Information

Molecular Structure:
CAS No.:	103255-66-9
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
Article Data:	5

Formula:	C₂₅H₂₃ClN₄O₄
Molecular Weight:	478.935
Synonyms:	1,4-Dioxa-8-azaspiro[4.5]decane,8-[[2-(7-chloro-1,8-naphthyridin-2-yl)-2,3-dihydro-3-oxo-1H-isoindol-1-yl]acetyl]-(9CI);(±)-2-(7-Chloro-1,8-naphthyridin-2-yl)-3-[(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)carbonylmethyl]isoindolin-1-one;A 77000;DN 2327;Pazinaclone;1,4-Dioxa-8-azaspiro(4.5)decane, 8-((2-(7-chloro-1,8-naphthyridin-2-yl)-2,3-dihydro-3-oxo-1H-isoindol-1-yl)acetyl)-, (±)-;1H-isoindol-1-one, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-[2-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-2-oxoethyl]-2,3-dihydro-;2-(7-chloro-1,8-naphthyridin-2-yl)-3-[2-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-2-oxoethyl]-2,3-dihydro-1H-isoindol-1-one;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;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;
Density:	1.48 g/cm³
Melting Point:	238-239°
Boiling Point:	712.5 °C at 760 mmHg
Flash Point:	384.7 °C
PSA:	84.86000
LogP:	3.74320

Synthetic route

: 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

: 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

Conditions	Yield
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%

: 104917-09-1
N-(7-chloro-1,8-naphthyridin-2-yl)benzamide

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

: 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

Conditions	Yield
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%

: 201230-82-2
carbon monoxide

: 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

: 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

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; trifuran-2-yl-phosphane; caesium carbonate In 1,4-dioxane at 110℃; under 760 Torr; Michael addition;	64%

...Expand

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

: 100-52-7
benzaldehyde

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

: 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

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In acetonitrile at 80℃; Inert atmosphere; Sealed tube;	20%

...Expand

: 103255-87-4
2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxoisoindoline-1-acetic acid

: 2942-58-7
diethyl cyanophosphonate

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

: 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

Conditions	Yield
With triethylamine In N-methyl-acetamide; water

...Expand

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

: 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

Conditions	Yield
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

Yield

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

: 3849-22-7
(3-oxo-2,3-dihydro-1H-isoindol-1-yl)-acetic acid

: 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

Conditions	Yield
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

Yield

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

: 33779-03-2
2-(2-methoxycarbonylethyl)benzoic acid

: 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

Conditions	Yield
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

Yield

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

: 98-88-4
benzoyl chloride

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

: 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

Conditions	Yield
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

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Specification

The Pazinaclone, with the CAS registry number 103255-66-9, has the systematic name of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-[2-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-2-oxoethyl]-2,3-dihydro-1H-isoindol-1-one. And the molecular formula of the chemical is C₂₅H₂₃ClN₄O₄.

The characteristics of Pazinaclone are as followings: (1)ACD/LogP: 2.34; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.34; (4)ACD/LogD (pH 7.4): 2.34; (5)ACD/BCF (pH 5.5): 35.17; (6)ACD/BCF (pH 7.4): 35.18; (7)ACD/KOC (pH 5.5): 444.99; (8)ACD/KOC (pH 7.4): 445.06; (9)#H bond acceptors: 8; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 84.86 Å²; (13)Index of Refraction: 1.709; (14)Molar Refractivity: 125.71 cm³; (15)Molar Volume: 321.9 cm³; (16)Polarizability: 49.83×10^-24cm³; (17)Surface Tension: 78.7 dyne/cm; (18)Density: 1.48 g/cm³; (19)Flash Point: 384.7 °C; (20)Enthalpy of Vaporization: 104.16 kJ/mol; (21)Boiling Point: 712.5 °C at 760 mmHg; (22)Vapour Pressure: 3.79E-20 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Clc1nc2nc(ccc2cc1)N4C(=O)c3ccccc3C4CC(=O)N6CCC5(OCCO5)CC6
(2)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
(3)InChIKey: DPGKFACWOCLTCA-UHFFFAOYAM

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LDLo	oral	1gm/kg (1000mg/kg)		United States Patent Document. Vol. #4695572