1,1-dimethylethyl 6-{5-[3-cyano-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Base Information

• Chemical Name: 1,1-dimethylethyl 6-{5-[3-cyano-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate
• CAS No.: 1286751-05-0
• Molecular Formula: C₂₇H₃₀N₄O₄
• Molecular Weight: 474.56
• Mol file: 1286751-05-0.mol

Synonyms:1,1-dimethylethyl 6-{5-[3-cyano-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Chemical Property of 1,1-dimethylethyl 6-{5-[3-cyano-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl 6-{5-[3-cyano-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

There total 12 articles about 1,1-dimethylethyl 6-{5-[3-cyano-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate 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: 82.0%

propan-1-ol (71-23-8) + 1,1-dimethylethyl 6-[5-(3-cyano-4-fluorophenyl)-1,2,4-oxadiazol-3-yl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (1286751-03-8) → 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)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ml2000214

Reference yield:

C18H31NO3Si → 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)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; palladium diacetate; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; 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) → 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)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/ml2000214

upstream raw materials:

propan-1-ol

1,1-dimethylethyl 6-[5-(3-cyano-4-fluorophenyl)-1,2,4-oxadiazol-3-yl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

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

Downstream raw materials:

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

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

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