Technology Process of N-{3-[(1R,2S,7R,8S)-3-(4-fluoro-3-methylbenzyl)-6-hydroxy-4-oxo-3-aza-tricyclo[6.2.1.02,7]undec-5-en-5-yl]-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}methanesulfonamide
There total 15 articles about N-{3-[(1R,2S,7R,8S)-3-(4-fluoro-3-methylbenzyl)-6-hydroxy-4-oxo-3-aza-tricyclo[6.2.1.02,7]undec-5-en-5-yl]-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}methanesulfonamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[e][1,2,4]thiadiazin-3-yl)-acetic acid; methyl (1S,2R,3S,4R)-3-[(4-fluoro-3-methylbenzyl)amino]bicyclo[2.2.1]heptane-2-carboxylate;
With
4-methyl-morpholine;
In
N,N-dimethyl-formamide;
for 0.0833333h;
With
1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
In
N,N-dimethyl-formamide;
at 25 ℃;
for 4h;
With
triethylamine;
In
N,N-dimethyl-formamide;
at 50 ℃;
for 16h;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: triethylamine / acetonitrile / 20 h / 92 °C / Industry scale
2.1: hydrogen / palladium 10% on activated carbon / ethanol; water; tetrahydrofuran / 43 h / 50 °C / 2844.39 Torr / Industry scale
3.1: pyridine / dichloromethane / 0 - 23 °C / Industry scale
4.1: tetrahydrofuran / 1 h / 0 - 23 °C / Industry scale
5.1: sodium hydroxide; water / 30 h / 23 °C / Industry scale
5.2: 0 °C / Industry scale
6.1: 4-methyl-morpholine / N,N-dimethyl-formamide / 0.08 h
6.2: 4 h / 25 °C
6.3: 16 h / 50 °C
With
4-methyl-morpholine; pyridine; water; hydrogen; triethylamine; sodium hydroxide;
palladium 10% on activated carbon;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: N,N-dimethyl-formamide; thionyl chloride / 4 h / Reflux
2.1: ammonium hydroxide / toluene; water; tetrahydrofuran / 2 h / -10 °C / Reflux
2.2: pH 4
3.1: ammonium hydroxide; ammonium carbonate; copper(II) sulfate / water / 72 h / 118 °C / Autoclave; Industry scale
4.1: hydrogen / 5%-palladium/activated carbon / ethanol; water / 8 h / 55 °C / Industry scale
5.1: pyridine / dichloromethane / 0 - 23 °C / Industry scale
6.1: tetrahydrofuran / 1 h / 0 - 23 °C / Industry scale
7.1: sodium hydroxide; water / 30 h / 23 °C / Industry scale
7.2: 0 °C / Industry scale
8.1: 4-methyl-morpholine / N,N-dimethyl-formamide / 0.08 h
8.2: 4 h / 25 °C
8.3: 16 h / 50 °C
With
4-methyl-morpholine; pyridine; ammonium hydroxide; thionyl chloride; water; hydrogen; ammonium carbonate; copper(II) sulfate; N,N-dimethyl-formamide; sodium hydroxide;
5%-palladium/activated carbon;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;