3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-(methylthio)pyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one

Base Information

Chemical Name:3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-(methylthio)pyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one
CAS No.:1227924-20-0
Molecular Formula:C₂₅H₂₅N₃O₂S
Molecular Weight:431.558
Hs Code.:

Synonyms:3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-(methylthio)pyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one

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Chemical Property of 3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-(methylthio)pyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one

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Technology Process of 3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-(methylthio)pyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one

There total 10 articles about 3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-(methylthio)pyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-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: 84.0%

: 1227923-94-5
6-((6-chloropyridin-3-yl)methyl)-3-((1S,2S)-2-hydroxycyclohexyl)benzo[h]quinazolin-4(3H)-one

: 5188-07-8
sodium thiomethoxide

: 1227924-20-0
3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-(methylthio)pyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one

Guidance literature:: With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 18h; Inert atmosphere;
DOI:10.1021/acsmedchemlett.8b00095

Reference yield:

: 931-15-7,931-16-8,6850-38-0,6982-39-4,33092-82-9,38898-70-3,74111-21-0,108267-20-5
(1S,2S)-trans-2-aminocyclohexanol

: 1227924-20-0
3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-(methylthio)pyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / 15 h / 20 °C / Inert atmosphere

2: 2 h / 80 °C / Inert atmosphere

3: bis(tri-t-butylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 0.25 h / 0 - 20 °C / Inert atmosphere

4: trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 18 h / 120 °C / Inert atmosphere

With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; bis(tri-t-butylphosphine)palladium⁽⁰⁾; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/acsmedchemlett.8b00095

Reference yield:

: 881-03-8
1-nitro-2-methylnaphthalene

: 1227924-20-0
3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-(methylthio)pyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one

Guidance literature:: Multi-step reaction with 10 steps

1: toluene / 39 h / 120 °C / Inert atmosphere

2: potassium carbonate; potassium permanganate / water; tert-butyl alcohol / 17.5 h / 20 °C / Inert atmosphere

3: hydrogenchloride / 42 h / 0 - 90 °C / Inert atmosphere

4: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol / 14 h / 760.05 Torr

5: bromine / tetrachloromethane; 1,4-dioxane / 2 h / 0 °C / Inert atmosphere

6: alkali metal hydroxide / tetrahydrofuran; water / 22 h / 50 - 90 °C / Inert atmosphere

7: triethylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / 15 h / 20 °C / Inert atmosphere

8: 2 h / 80 °C / Inert atmosphere

9: bis(tri-t-butylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 0.25 h / 0 - 20 °C / Inert atmosphere

10: trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 18 h / 120 °C / Inert atmosphere

With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; hydrogenchloride; potassium permanganate; copper(l) iodide; bis(tri-t-butylphosphine)palladium⁽⁰⁾; palladium on activated charcoal; hydrogen; bromine; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/acsmedchemlett.8b00095