Technology Process of 5-but-2-ynyloxypyrazine-2-carboxylic acid [3-((4S,4aR,7aR)-2-amino-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-4-yl)-4-fluorophenyl]amide
There total 10 articles about 5-but-2-ynyloxypyrazine-2-carboxylic acid [3-((4S,4aR,7aR)-2-amino-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-4-yl)-4-fluorophenyl]amide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
5-(but-2-yn-1-yloxy)pyrazine-2-carboxylic acid;
With
4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride;
In
methanol;
at 0 ℃;
for 0.0833333h;
(4S,4aR,7aR)-4-(5-amino-2-fluorophenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine;
In
methanol;
at 0 - 20 ℃;
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: triethylamine; phenyl isocyanate / diethyl ether / 25 °C / Inert atmosphere
2.1: morpholinosulfur trifluoride / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1.17 h / 70 - 78 °C / Inert atmosphere
3.2: 2.17 h / 70 - 78 °C
4.1: n-heptane; ethanol / Resolution of racemate
5.1: palladium 10% on activated carbon; ammonium formate / ethanol / 2.5 h / 22 °C
6.1: ethanol / acetonitrile / 22 h / 85 °C / Sealed tube
7.1: sulfuric acid; nitric acid / 2 h / 0 - 22 °C
8.1: triethylamine; palladium 10% on activated carbon; hydrogen / ethanol / 1.5 h / 22 °C / 760.05 Torr
9.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 0.08 h / 0 °C
9.2: 0 - 20 °C
With
n-butyllithium; ethanol; sulfuric acid; palladium 10% on activated carbon; hydrogen; nitric acid; ammonium formate; phenyl isocyanate; triethylamine; morpholinosulfur trifluoride; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; n-heptane; dichloromethane; toluene; acetonitrile;
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: ethanol / acetonitrile / 22 h / 85 °C / Sealed tube
2.1: sulfuric acid; nitric acid / 2 h / 0 - 22 °C
3.1: triethylamine; palladium 10% on activated carbon; hydrogen / ethanol / 1.5 h / 22 °C / 760.05 Torr
4.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 0.08 h / 0 °C
4.2: 0 - 20 °C
With
ethanol; sulfuric acid; palladium 10% on activated carbon; hydrogen; nitric acid; triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride;
In
methanol; ethanol; acetonitrile;
