Technology Process of 4-{7-[3-Methoxy-5-((S)-2-methyl-pyrrolidin-1-yl)-phenylamino]-thiazolo[5,4-d]pyrimidin-5-yl}-benzamide
There total 7 articles about 4-{7-[3-Methoxy-5-((S)-2-methyl-pyrrolidin-1-yl)-phenylamino]-thiazolo[5,4-d]pyrimidin-5-yl}-benzamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(S)-4-(7-(3-methoxy-5-(2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid;
With
benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
In
dichloromethane;
at 20 ℃;
for 3h;
With
ammonia;
In
dichloromethane;
for 3h;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
2.1: hydrogenchloride / zinc / 1,4-dioxane; water / 2 h / 20 °C
2.2: pH 8
3.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 16 h / 30 °C
4.1: sodium carbonate; XPhos / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; water / 16 h / 100 °C / Inert atmosphere
5.1: sodium hydroxide; water / 1,4-dioxane / 2 h / 30 °C
5.2: pH 4
6.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 3 h / 20 °C
6.2: 3 h
With
hydrogenchloride; water; sodium carbonate; benzotriazol-1-ol; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; XPhos;
tris-(dibenzylideneacetone)dipalladium(0); zinc;
In
1,4-dioxane; dichloromethane; water; dimethyl sulfoxide;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
2.1: hydrogenchloride / zinc / 1,4-dioxane; water / 2 h / 20 °C
2.2: pH 8
3.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 16 h / 30 °C
4.1: sodium carbonate; XPhos / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; water / 16 h / 100 °C / Inert atmosphere
5.1: sodium hydroxide; water / 1,4-dioxane / 2 h / 30 °C
5.2: pH 4
6.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 3 h / 20 °C
6.2: 3 h
With
hydrogenchloride; water; sodium carbonate; benzotriazol-1-ol; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; XPhos;
tris-(dibenzylideneacetone)dipalladium(0); zinc;
In
1,4-dioxane; dichloromethane; water; dimethyl sulfoxide;