Technology Process of 2,2-dimethyl-N-(5-methylpyridin-3-yl)-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-2H-pyrido[3,2-b][1,4]oxazine-4(3H)-carboxamide
There total 9 articles about 2,2-dimethyl-N-(5-methylpyridin-3-yl)-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-2H-pyrido[3,2-b][1,4]oxazine-4(3H)-carboxamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
bis(trichloromethyl) carbonate; 2,2-dimethyl-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine;
With
triethylamine;
In
tetrahydrofuran;
at 20 ℃;
for 0.5h;
5-methylpyridin-3-amine;
In
tetrahydrofuran;
at 60 ℃;
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: sodium methylate; bromine / methanol / 0.5 h / 0 °C
1.2: 0.17 h / 0 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C
3.1: acetic acid; iron / 2 h / 90 °C
4.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / Reflux
4.2: 0.5 h / Reflux
5.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane / 90 °C / Inert atmosphere
6.1: lithium hydroxide monohydrate / water; tetrahydrofuran; methanol / 1 h / 20 °C
6.2: 20 °C / pH 3 - 4
7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C
8.1: dimethylsulfide borane complex / tetrahydrofuran / 18 h / Reflux
8.2: 1 h / Reflux
9.1: triethylamine / tetrahydrofuran / 0.5 h / 20 °C
9.2: 60 °C
With
lithium hydroxide monohydrate; dimethylsulfide borane complex; bromine; sodium methylate; iron; potassium carbonate; caesium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; HATU;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C
2.1: acetic acid; iron / 2 h / 90 °C
3.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / Reflux
3.2: 0.5 h / Reflux
4.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane / 90 °C / Inert atmosphere
5.1: lithium hydroxide monohydrate / water; tetrahydrofuran; methanol / 1 h / 20 °C
5.2: 20 °C / pH 3 - 4
6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C
7.1: dimethylsulfide borane complex / tetrahydrofuran / 18 h / Reflux
7.2: 1 h / Reflux
8.1: triethylamine / tetrahydrofuran / 0.5 h / 20 °C
8.2: 60 °C
With
lithium hydroxide monohydrate; dimethylsulfide borane complex; iron; potassium carbonate; caesium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; HATU;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide;
