14,14-dimethyl-8-[(4-methylbenzene)sulfonyl]-8,10,13-triazatetracyclo-[7.7.0.02,7.011,15]hexadeca-1⁽¹⁶⁾,2⁽⁷⁾,3,5,9,11⁽¹⁵⁾-hexaen-12-one

Base Information

• Chemical Name: 14,14-dimethyl-8-[(4-methylbenzene)sulfonyl]-8,10,13-triazatetracyclo-[7.7.0.02,7.011,15]hexadeca-1⁽¹⁶⁾,2⁽⁷⁾,3,5,9,11⁽¹⁵⁾-hexaen-12-one
• CAS No.: 1394236-94-2
• Molecular Formula: C₂₂H₁₉N₃O₃S
• Molecular Weight: 405.477

Synonyms:14,14-dimethyl-8-[(4-methylbenzene)sulfonyl]-8,10,13-triazatetracyclo-[7.7.0.02,7.011,15]hexadeca-1⁽¹⁶⁾,2⁽⁷⁾,3,5,9,11⁽¹⁵⁾-hexaen-12-one

Chemical Property of 14,14-dimethyl-8-[(4-methylbenzene)sulfonyl]-8,10,13-triazatetracyclo-[7.7.0.02,7.011,15]hexadeca-1⁽¹⁶⁾,2⁽⁷⁾,3,5,9,11⁽¹⁵⁾-hexaen-12-one

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Technology Process of 14,14-dimethyl-8-[(4-methylbenzene)sulfonyl]-8,10,13-triazatetracyclo-[7.7.0.02,7.011,15]hexadeca-1⁽¹⁶⁾,2⁽⁷⁾,3,5,9,11⁽¹⁵⁾-hexaen-12-one

There total 4 articles about 14,14-dimethyl-8-[(4-methylbenzene)sulfonyl]-8,10,13-triazatetracyclo-[7.7.0.02,7.011,15]hexadeca-1⁽¹⁶⁾,2⁽⁷⁾,3,5,9,11⁽¹⁵⁾-hexaen-12-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: 91.0%

5-[(4-methylbenzene)sulfonyl]-N-(2-methylbut-3-yn-2-yl)-5H-[1,2,4]triazino[5,6-b]indole-3-carboxamide (1394237-99-0) → 14,14-dimethyl-8-[(4-methylbenzene)sulfonyl]-8,10,13-triazatetracyclo-[7.7.0.02,7.011,15]hexadeca-1(16),2(7),3,5,9,11(15)-hexaen-12-one (1394236-94-2)

Guidance literature:

In diethylene glycol dimethyl ether; at 160 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

DOI:10.3762/bjoc.8.93

Reference yield:

ethyl 5-[(4-methylbenzene)sulfonyl]-5H-[1,2,4]triazino[5,6-b]indole-3-carboxylate (1394237-82-1) → 14,14-dimethyl-8-[(4-methylbenzene)sulfonyl]-8,10,13-triazatetracyclo-[7.7.0.02,7.011,15]hexadeca-1(16),2(7),3,5,9,11(15)-hexaen-12-one (1394236-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1: zirconium(IV) tert-butoxide / dichloromethane / 16 h / 20 °C / Inert atmosphere

2: diethylene glycol dimethyl ether / 0.5 h / 160 °C / Inert atmosphere; Microwave irradiation

With zirconium(IV) tert-butoxide; In dichloromethane; diethylene glycol dimethyl ether; 2: Inverse electron demand Diels-Alder reaction;

DOI:10.3762/bjoc.8.93

Reference yield:

C12H10N4O2 (1394237-93-4) → 14,14-dimethyl-8-[(4-methylbenzene)sulfonyl]-8,10,13-triazatetracyclo-[7.7.0.02,7.011,15]hexadeca-1(16),2(7),3,5,9,11(15)-hexaen-12-one (1394236-94-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

1.2: 7 h / 20 °C / Inert atmosphere

2.1: zirconium(IV) tert-butoxide / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: diethylene glycol dimethyl ether / 0.5 h / 160 °C / Inert atmosphere; Microwave irradiation

With zirconium(IV) tert-butoxide; triethylamine; In tetrahydrofuran; dichloromethane; diethylene glycol dimethyl ether; 3.1: Inverse electron demand Diels-Alder reaction;

DOI:10.3762/bjoc.8.93

upstream raw materials:

ethyl 5-[(4-methylbenzene)sulfonyl]-5H-[1,2,4]triazino[5,6-b]indole-3-carboxylate

5-[(4-methylbenzene)sulfonyl]-N-(2-methylbut-3-yn-2-yl)-5H-[1,2,4]triazino[5,6-b]indole-3-carboxamide

C₁₂H₁₀N₄O₂

indole-2,3-dione

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