2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile

Base Information

• Chemical Name: 2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile
• CAS No.: 1258440-17-3
• Molecular Formula: C₂₁H₂₀N₄OS
• Molecular Weight: 376.482
• Mol file: 1258440-17-3.mol

Synonyms:2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile

Chemical Property of 2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile

There total 11 articles about 2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile 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:

1,1-dimethylethyl 6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate (1258440-75-3) → 2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile (1258440-17-3)

Guidance literature:

1,1-dimethylethyl 6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere;

With ammonia; In methanol; SCX cartridge;

Reference yield:

3-cyano-4-isopropoxybenzoic acid (258273-31-3) → 2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile (1258440-17-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trichlorophosphate / 3 h / 90 °C

1.2: 35 °C / pH 10 / Cooling with ice

2.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 20 - 70 °C

3.1: sodium hydrogencarbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 5 h / 90 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

With tert.-butylnitrite; sodium hydrogencarbonate; trifluoroacetic acid; copper(ll) bromide; trichlorophosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; dichloromethane; acetonitrile;

Reference yield:

salicylonitrile (611-20-1) → 2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile (1258440-17-3)

Guidance literature:

Multi-step reaction with 6 steps

1: trifluorormethanesulfonic acid; N-iodo-succinimide / acetonitrile / 0 - 20 °C

2: potassium carbonate / acetonitrile / Reflux

3: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 90 °C / Inert atmosphere

4: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / Reflux; Inert atmosphere

5: sodium hydrogencarbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 5 h / 90 °C / Inert atmosphere

6: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

With N-iodo-succinimide; trifluorormethanesulfonic acid; potassium acetate; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; trifluoroacetic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; water; acetonitrile;

upstream raw materials:

1,1-dimethylethyl 6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate

salicylonitrile

3-cyano-4-isopropoxybenzoic acid

2-hydroxy-5-iodobenzonitrile

Downstream raw materials:

3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanamide