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

Base Information

• Chemical Name: 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanamide
• CAS No.: 1258852-58-2
• Molecular Formula: C₂₄H₂₅N₅O₂S
• Molecular Weight: 447.561
• Mol file: 1258852-58-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanamide 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:

2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile (1258440-17-3) + 2-propenamide (79-06-1,12624-24-7,25038-45-3,27754-57-0,33338-03-3,39387-77-4,68247-81-4,9082-06-8,79079-15-5) → 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanamide (1258852-58-2)

Guidance literature:

With silica gel; In acetonitrile; at 60 ℃; for 6h; Inert atmosphere;

Reference yield:

salicylonitrile (611-20-1) → 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanamide (1258852-58-2)

Guidance literature:

Multi-step reaction with 7 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

7: silica gel / acetonitrile / 6 h / 60 °C / Inert atmosphere

With N-iodo-succinimide; trifluorormethanesulfonic acid; potassium acetate; silica gel; 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;

Reference yield:

3-cyano-4-isopropoxybenzoic acid (258273-31-3) → 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanamide (1258852-58-2)

Guidance literature:

Multi-step reaction with 5 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

5.1: silica gel / acetonitrile / 6 h / 60 °C / Inert atmosphere

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

upstream raw materials:

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

2-propenamide

salicylonitrile

3-cyano-4-isopropoxybenzoic acid