5-(3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-propoxybenzonitrile hydrochloride

Base Information

• Chemical Name: 5-(3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-propoxybenzonitrile hydrochloride
• CAS No.: 1286751-06-1
• Molecular Formula: C₂₂H₂₂N₄O₂*ClH
• Molecular Weight: 410.903
• Mol file: 1286751-06-1.mol

Synonyms:5-(3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-propoxybenzonitrile hydrochloride

Chemical Property of 5-(3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-propoxybenzonitrile hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-propoxybenzonitrile hydrochloride

There total 10 articles about 5-(3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-propoxybenzonitrile hydrochloride 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: 98.0%

1,1-dimethylethyl 6-{5-[3-cyano-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (1286751-05-0) → 5-(3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-propoxybenzonitrile hydrochloride (1286751-06-1)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ml2000214

Reference yield:

C18H31NO3Si → 5-(3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-propoxybenzonitrile hydrochloride (1286751-06-1)

Guidance literature:

Multi-step reaction with 8 steps

1: palladium diacetate / acetonitrile / 35 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran; ethyl acetate / 0.5 h

3: pyridine / dichloromethane / -30 - 20 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 6 h / 100 °C / Inert atmosphere

5: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 28.5 h / Reflux

6: pyridine / toluene / 3 h / 20 - 110 °C / Inert atmosphere

7: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere

8: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; palladium diacetate; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;

DOI:10.1021/ml2000214

Reference yield:

1,1-dimethylethyl 6-hydroxy-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (1165923-89-6) → 5-(3-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-propoxybenzonitrile hydrochloride (1286751-06-1)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / dichloromethane / -30 - 20 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 6 h / 100 °C / Inert atmosphere

3: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 28.5 h / Reflux

4: pyridine / toluene / 3 h / 20 - 110 °C / Inert atmosphere

5: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere

6: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydroxylamine hydrochloride; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1021/ml2000214

upstream raw materials:

1,1-dimethylethyl 6-hydroxy-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

1,1-dimethylethyl 5-methyl-6-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2(1H)-isoquinolinecarboxylate

1,1-dimethylethyl 6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

1,1-dimethylethyl 6-[(hydroxyamino)(imino)methyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Downstream raw materials:

sodium 3-[6-(5-(3-cyano-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoate

ethyl 3-(6-(5-(3-cyano-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl)propanoate