Technology Process of (S,E)-4-(2-(3-(3-chloro-2-fluoro-6-(1H-tetrazol-1-yl)phenyl)acryloyl)-5-(1,1-dioxidothiomorpholino)-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzoic acid
There total 13 articles about (S,E)-4-(2-(3-(3-chloro-2-fluoro-6-(1H-tetrazol-1-yl)phenyl)acryloyl)-5-(1,1-dioxidothiomorpholino)-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzoic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
carbon dioxide;
In
ethanol; diethylamine; isopropyl alcohol;
at 35 ℃;
under 75007.5 Torr;
Resolution of racemate;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: sodium carbonate / diethyl ether / 1 h / -10 °C
2.1: tert.-butyl lithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; pentane / 1 h / -78 °C
2.2: 1.5 h
3.1: 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 110 °C
4.1: sodium hydroxide / ethanol; water / 1 h / 80 °C
4.2: 0 °C / pH 6 - 7
5.1: acetic acid; sodium azide / 4 h / 75 °C
6.1: methanol / 72 h / 55 °C / Sealed tube
7.1: Chiralpak AD-H / ethanol; isopropyl alcohol; diethylamine / Resolution of racemate
8.1: trifluoroacetic acid / dichloromethane / 3 h
With
1,4-diaza-bicyclo[2.2.2]octane; sodium azide; N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; palladium diacetate; sodium carbonate; potassium carbonate; acetic acid; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; diethylamine; N,N-dimethyl-formamide; isopropyl alcohol; pentane;
6.1: |Ugi Condensation;
DOI:10.1021/acs.jmedchem.7b01171
- Guidance literature:
-
Multi-step reaction with 5 steps
1: neat (no solvent) / 24 h / Reflux
2: trichlorophosphate; triethylamine / tetrahydrofuran / 2 h / 0 °C
3: methanol / 72 h / 55 °C / Sealed tube
4: Chiralpak AD-H / ethanol; isopropyl alcohol; diethylamine / Resolution of racemate
5: trifluoroacetic acid / dichloromethane / 3 h
With
triethylamine; trifluoroacetic acid; trichlorophosphate;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; diethylamine; isopropyl alcohol;
3: |Ugi Condensation;
DOI:10.1021/acs.jmedchem.7b01171
