Technology Process of N-(((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)methyl)acetamide
There total 18 articles about N-(((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)methyl)acetamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
2-((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6Hisoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)acetic acid;
With
diphenylphosphoranyl azide; triethylamine;
In
toluene;
at 80 - 90 ℃;
for 0.5h;
With
sodium hydroxide;
In
1,4-dioxane;
at 90 ℃;
for 1h;
acetic anhydride;
With
triethylamine;
In
1,4-dioxane;
for 1h;
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: isopropylmagnesium bromide / tetrahydrofuran; cyclopentyl methyl ether / -20 - 0 °C
2.1: diethyl ether; tetrahydrofuran / 0.17 h / -40 °C
3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h
4.1: potassium carbonate; water / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 5 h / 95 °C / Inert atmosphere
5.1: oxalyl dichloride / dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
6.1: titanium(IV) ethoxide / dichloromethane / 24 h
7.1: tetrahydrofuran / 0 °C
8.1: hydrogenchloride; methanol / 1,4-dioxane / 0.5 h
8.2: 24 h / Reflux
9.1: triethylamine; diphenylphosphoranyl azide / toluene / 0.5 h / 80 - 90 °C
9.2: 1 h / 90 °C
9.3: 1 h
With
hydrogenchloride; methanol; N-Bromosuccinimide; oxalyl dichloride; diphenylphosphoranyl azide; water; isopropylmagnesium bromide; potassium carbonate; triethylamine;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; titanium(IV) ethoxide; dimethyl sulfoxide;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; cyclopentyl methyl ether; N,N-dimethyl-formamide; toluene;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: N-Bromosuccinimide / sulfuric acid / acetic acid / 1 h / 110 °C
1.2: 20 °C / pH 8 - 9
2.1: triethylamine / dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II) / 4 h / 110 °C / Inert atmosphere
3.1: potassium carbonate; water / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 5 h / 95 °C / Inert atmosphere
4.1: oxalyl dichloride / dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
5.1: titanium(IV) ethoxide / dichloromethane / 24 h
6.1: tetrahydrofuran / 0 °C
7.1: hydrogenchloride; methanol / 1,4-dioxane / 0.5 h
7.2: 24 h / Reflux
8.1: triethylamine; diphenylphosphoranyl azide / toluene / 0.5 h / 80 - 90 °C
8.2: 1 h / 90 °C
8.3: 1 h
With
hydrogenchloride; methanol; N-Bromosuccinimide; oxalyl dichloride; diphenylphosphoranyl azide; water; potassium carbonate; triethylamine;
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sulfuric acid; titanium(IV) ethoxide; dimethyl sulfoxide;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid; toluene;