Technology Process of (4-{1-(4,4-difluorocyclohexylcarbonylamino)-3-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]propyl}phenyl)carbamic acid tert-butyl ester
There total 10 articles about (4-{1-(4,4-difluorocyclohexylcarbonylamino)-3-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]propyl}phenyl)carbamic acid tert-butyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
4,4-difluorocyclohexanecarboxylic acid;
With
benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
In
dichloromethane;
for 0.25h;
Inert atmosphere;
Cooling with ice;
Molecular sieve;
(4-{1-amino-3-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]propyl}phenyl)carbamic acid tert-butyl ester;
In
dichloromethane;
at 20 ℃;
for 4h;
Inert atmosphere;
Molecular sieve;
DOI:10.1039/c2ob06801j
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 0.25 h / Inert atmosphere; Cooling with ice; Molecular sieve
1.2: 4 h / 20 °C / Inert atmosphere; Molecular sieve
2.1: palladium 10% on activated carbon; hydrogen / methanol / 96 h / 20 °C / 3102.97 Torr
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.25 h / 20 °C / Cooling with ice
4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 0.25 h / Inert atmosphere; Cooling with ice; Molecular sieve
4.2: 4 h / 20 °C / Inert atmosphere; Molecular sieve
With
lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1039/c2ob06801j
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: tetrahydrofuran / Reflux
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / Inert atmosphere; Cooling with ice
2.2: 2 h / -78 °C / Inert atmosphere
3.1: lithium hydroxide / methanol; water / 48 h / Reflux
4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 0.25 h / Inert atmosphere; Cooling with ice; Molecular sieve
4.2: 4 h / 20 °C / Inert atmosphere; Molecular sieve
5.1: palladium 10% on activated carbon; hydrogen / methanol / 96 h / 20 °C / 3102.97 Torr
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.25 h / 20 °C / Cooling with ice
7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 0.25 h / Inert atmosphere; Cooling with ice; Molecular sieve
7.2: 4 h / 20 °C / Inert atmosphere; Molecular sieve
With
lithium aluminium tetrahydride; n-butyllithium; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1039/c2ob06801j