Technology Process of (6R)-3'-methyl-N-[(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,5,6-tetrafluorophenyl)piperidin-3-yl]-2',5'-dioxo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,4'-imidazolidine]-3-carboxamide
There total 7 articles about (6R)-3'-methyl-N-[(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,5,6-tetrafluorophenyl)piperidin-3-yl]-2',5'-dioxo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,4'-imidazolidine]-3-carboxamide 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:
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1401065-97-1
(6R)-3'-methyl-N-[(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,5,6-tetrafluorophenyl)piperidin-3-yl]-2',5'-dioxo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,4'-imidazolidine]-3-carboxamide
- Guidance literature:
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With
benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 6h;
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1401065-97-1
(6R)-3'-methyl-N-[(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,5,6-tetrafluorophenyl)piperidin-3-yl]-2',5'-dioxo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,4'-imidazolidine]-3-carboxamide
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: sodium hydride / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrahydrofuran / 0.17 h / 0 °C
1.2: 0 - 10 °C
2.1: sodium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 72 h / 80 °C / 15514.9 Torr / Inert atmosphere; Autoclave
3.1: ChiralPak.(R). IC column / acetonitrile; ethanol; carbon dioxide / Resolution of racemate
4.1: water; ammonium cerium (IV) nitrate; methanol / 18 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 2 h / 20 °C
5.2: pH 4
6.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 6 h / 20 °C
With
methanol; ammonium cerium (IV) nitrate; water; sodium acetate; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ethanol; carbon dioxide; water; N,N-dimethyl-formamide; acetonitrile;
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1401065-97-1
(6R)-3'-methyl-N-[(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,5,6-tetrafluorophenyl)piperidin-3-yl]-2',5'-dioxo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,4'-imidazolidine]-3-carboxamide
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / 0 - 35 °C
2.1: sodium hydride / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrahydrofuran / 0.17 h / 0 °C
2.2: 0 - 10 °C
3.1: sodium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 72 h / 80 °C / 15514.9 Torr / Inert atmosphere; Autoclave
4.1: ChiralPak.(R). IC column / acetonitrile; ethanol; carbon dioxide / Resolution of racemate
5.1: water; ammonium cerium (IV) nitrate; methanol / 18 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 2 h / 20 °C
6.2: pH 4
7.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 6 h / 20 °C
With
methanol; thionyl chloride; ammonium cerium (IV) nitrate; water; sodium acetate; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ethanol; carbon dioxide; water; N,N-dimethyl-formamide; acetonitrile;