[6-(4-Cyano-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester

Base Information

• Chemical Name: [6-(4-Cyano-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester
• CAS No.: 164147-80-2
• Molecular Formula: C₂₃H₂₃N₃O₄
• Molecular Weight: 405.453

Synonyms:[6-(4-Cyano-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester

Chemical Property of [6-(4-Cyano-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of [6-(4-Cyano-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester

There total 11 articles about [6-(4-Cyano-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 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: 96.0%

4-cyanobenzoic Acid (619-65-8,333406-09-0) + 6-amino-3,4-dihydro-1-oxo-2(1H)-isoquinolineacetic acid 1,1-dimethylethyl ester (164147-79-9) → [6-(4-Cyano-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester (164147-80-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jm9701076

Reference yield:

6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one (22245-98-3) → [6-(4-Cyano-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester (164147-80-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / K₂CO₃ / acetone / 16 h / Heating

2: 1.) NaH / 1.) THF, reflux, 2 h, 2.) THF, RT, 1 h

3: 95 percent / H₂ / 10percent Pd/C / ethyl acetate / 1.5 h

4: 82 percent / pyridine / 0 - 20 °C

5: 72 percent / palladium(II) acetate, Ph₃P, Et₃N / dimethylformamide / 15 h / 65 °C

6: 85 percent / 0.1 N aq. LiOH / tetrahydrofuran / 12 h / Ambient temperature

7: diphenyl phosphorazidate, Et₃N / toluene / 2 h / 85 °C

8: toluene / 1 h / Ambient temperature

9: 95 percent / 10percent Pd/C / ethanol; ethyl acetate / 1 h

10: 96 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; dmap; lithium hydroxide; palladium on activated charcoal; diphenyl phosphoryl azide; hydrogen; palladium diacetate; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jm9701076

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → [6-(4-Cyano-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester (164147-80-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1.) THF, reflux, 2 h, 2.) THF, RT, 1 h

2: 95 percent / H₂ / 10percent Pd/C / ethyl acetate / 1.5 h

3: 82 percent / pyridine / 0 - 20 °C

4: 72 percent / palladium(II) acetate, Ph₃P, Et₃N / dimethylformamide / 15 h / 65 °C

5: 85 percent / 0.1 N aq. LiOH / tetrahydrofuran / 12 h / Ambient temperature

6: diphenyl phosphorazidate, Et₃N / toluene / 2 h / 85 °C

7: toluene / 1 h / Ambient temperature

8: 95 percent / 10percent Pd/C / ethanol; ethyl acetate / 1 h

9: 96 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; dmap; lithium hydroxide; palladium on activated charcoal; diphenyl phosphoryl azide; hydrogen; palladium diacetate; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm9701076

upstream raw materials:

4-cyanobenzoic Acid

6-amino-3,4-dihydro-1-oxo-2(1H)-isoquinolineacetic acid 1,1-dimethylethyl ester

6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

bromoacetic acid tert-butyl ester

Downstream raw materials:

[1-Oxo-6-(4-thiocarbamoyl-benzoylamino)-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester

[6-(4-Methylsulfanylcarbonimidoyl-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester

{6-[4-(tert-Butoxycarbonylamino-imino-methyl)-benzoylamino]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid tert-butyl ester

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