1-(4-methoxybenzyl)-8-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-5,6,7,8-tetrahydro pyrazolo[3,4-b]azepin-4(1H)-one

Base Information

• Chemical Name: 1-(4-methoxybenzyl)-8-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-5,6,7,8-tetrahydro pyrazolo[3,4-b]azepin-4(1H)-one
• CAS No.: 1448437-87-3
• Molecular Formula: C₁₉H₂₁N₅O₃
• Molecular Weight: 367.407
• Mol file: 1448437-87-3.mol

Synonyms:1-(4-methoxybenzyl)-8-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-5,6,7,8-tetrahydro pyrazolo[3,4-b]azepin-4(1H)-one

Chemical Property of 1-(4-methoxybenzyl)-8-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-5,6,7,8-tetrahydro pyrazolo[3,4-b]azepin-4(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(4-methoxybenzyl)-8-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-5,6,7,8-tetrahydro pyrazolo[3,4-b]azepin-4(1H)-one

There total 11 articles about 1-(4-methoxybenzyl)-8-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-5,6,7,8-tetrahydro pyrazolo[3,4-b]azepin-4(1H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

3-(chloromethyl)-5-methyl-1,2,4-oxadiazole (1192-80-9) + 1-(4-methoxybenzyl)-5,6,7,8-tetrahydropyrazolo[3,4-b]azepin-4(1H)-one → 1-(4-methoxybenzyl)-8-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-5,6,7,8-tetrahydro pyrazolo[3,4-b]azepin-4(1H)-one (1448437-87-3)

Guidance literature:

1-(4-methoxybenzyl)-5,6,7,8-tetrahydropyrazolo[3,4-b]azepin-4(1H)-one; With 15-crown-5; sodium t-butanolate; In tetrahydrofuran; at 20 ℃; for 0.166667h; Inert atmosphere;

3-(chloromethyl)-5-methyl-1,2,4-oxadiazole; In tetrahydrofuran; for 2h; Reflux;

Reference yield:

N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide (1105039-59-5) → 1-(4-methoxybenzyl)-8-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-5,6,7,8-tetrahydro pyrazolo[3,4-b]azepin-4(1H)-one (1448437-87-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium diisopropyl amide / water; tetrahydrofuran / 1.67 h / -78 - -40 °C / Inert atmosphere

1.2: 2 h / -78 °C

2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate; palladium diacetate / 1,4-dioxane / 8 h / 110 °C / Inert atmosphere

3.1: sodium hydride / water; tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

3.2: 0.5 h / 20 °C

4.1: water; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

5.1: Grubbs catalyst first generation / 1,2-dichloro-ethane / 5 h / 20 °C / Reflux; Inert atmosphere

6.1: acetic acid; palladium(II) hydroxide; hydrogen / ethanol / 6 h / 20 °C / Inert atmosphere

7.1: 15-crown-5; sodium t-butanolate / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

7.2: 2 h / Reflux

With Grubbs catalyst first generation; 15-crown-5; hydrogen; palladium diacetate; palladium(II) hydroxide; sodium hydride; caesium carbonate; acetic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 2.1: |Buchwald-Hartwig Coupling;

Reference yield:

5-(benzylamino)-N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide (1448437-67-9) → 1-(4-methoxybenzyl)-8-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-5,6,7,8-tetrahydro pyrazolo[3,4-b]azepin-4(1H)-one (1448437-87-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / water; tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 20 °C

2.1: water; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.1: Grubbs catalyst first generation / 1,2-dichloro-ethane / 5 h / 20 °C / Reflux; Inert atmosphere

4.1: acetic acid; palladium(II) hydroxide; hydrogen / ethanol / 6 h / 20 °C / Inert atmosphere

5.1: 15-crown-5; sodium t-butanolate / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

5.2: 2 h / Reflux

With Grubbs catalyst first generation; 15-crown-5; hydrogen; palladium(II) hydroxide; sodium hydride; acetic acid; sodium t-butanolate; In tetrahydrofuran; ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

upstream raw materials:

N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide

5-bromo-N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide

5-(benzylamino)-N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide

5-(allyl(benzyl)amino)-N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide

Downstream raw materials:

N-(5-fluoropyrimidin-2-yl)-7-(4-methoxybenzyl)-6-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-4,5,6,7-tetrahydropyrazolo[3,4-b]thiazolo[4,5-d]azepin-2-amine

Refernces

• 1、 -. "NOVEL 2-AMINO-4,5,6,8-TETRAHYDROPYRAZOLO[3,4-b]THIAZOLO [4,5-d]AZEPINE DERIVATIVES AND THEIR USE AS ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS". . . Retrieved 2013/07/31.