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

Base Information

• Chemical Name: 3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-methoxypyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one
• CAS No.: 1227924-28-8
• Molecular Formula: C₂₅H₂₅N₃O₃
• Molecular Weight: 415.492
• Mol file: 1227924-28-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-methoxypyridin-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: 10.0%

methanol (67-56-1) + 6-((6-chloropyridin-3-yl)methyl)-3-((1S,2S)-2-hydroxycyclohexyl)benzo[h]quinazolin-4(3H)-one (1227923-94-5) → 3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-methoxypyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one (1227924-28-8)

Guidance literature:

With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; caesium carbonate; In water; at 160 ℃; for 1h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/acsmedchemlett.8b00095

Reference yield:

(1S,2S)-trans-2-aminocyclohexanol (931-15-7,931-16-8,6850-38-0,6982-39-4,33092-82-9,38898-70-3,74111-21-0,108267-20-5) → 3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-methoxypyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one (1227924-28-8)

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 / water / 1 h / 160 °C / Inert atmosphere; Microwave irradiation

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; water;

DOI:10.1021/acsmedchemlett.8b00095

Reference yield:

1-nitro-2-methylnaphthalene (881-03-8) → 3-((1S,2S)-2-hydroxycyclohexyl)-6-((6-methoxypyridin-3-yl)methyl)benzo[h]quinazolin-4(3H)-one (1227924-28-8)

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 / water / 1 h / 160 °C / Inert atmosphere; Microwave irradiation

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; toluene; tert-butyl alcohol;

DOI:10.1021/acsmedchemlett.8b00095

upstream raw materials:

(1S,2S)-trans-2-aminocyclohexanol

1-nitro-2-methylnaphthalene

1-nitro-2-naphthoic acid

methanol

Refernces