(6S)-6-((1H-imidazol-2-yl)methyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepine

Base Information

Chemical Name:(6S)-6-((1H-imidazol-2-yl)methyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepine
CAS No.:1380088-44-7
Molecular Formula:C₂₂H₁₉ClN₄OS
Molecular Weight:422.938
Hs Code.:

Synonyms:

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Chemical Property of (6S)-6-((1H-imidazol-2-yl)methyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepine

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Technology Process of (6S)-6-((1H-imidazol-2-yl)methyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepine

There total 12 articles about (6S)-6-((1H-imidazol-2-yl)methyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 6.2%

: 1380089-76-8
2-((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)ethanethioamide

: 22483-09-6
2,2-dimethoxyethylamine

: 1380088-44-7
(6S)-6-((1H-imidazol-2-yl)methyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepine

Guidance literature:: With mercury dichloride; In acetonitrile; Reflux;
DOI:10.1021/ml4001485

Reference yield:

: 1019115-42-4
methyl 2-bromo-4,5-dimethylthiophene-3-carboxylate

: 1380088-44-7
(6S)-6-((1H-imidazol-2-yl)methyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepine

Guidance literature:: Multi-step reaction with 13 steps

1.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate / 1,4-dioxane; butan-1-ol / 1 h / 100 °C / Inert atmosphere

2.1: sodium methylate; methanol / 1.5 h

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

3.2: -78 - 20 °C

4.1: titanium(IV) tetraethanolate / dichloromethane / 24 h / 20 °C

5.1: 1-methyl-pyrrolidin-2-one; diethyl ether / 6.17 h / -8.5 - 5 °C

6.1: hydrogenchloride / 1,4-dioxane; methanol / 0.25 h / 20 °C

7.1: isopropylmagnesium bromide / tetrahydrofuran; 2-methyltetrahydrofuran / -20 - 20 °C

8.1: phosphorus pentachloride / dichloromethane / 1.5 h / 20 °C

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / toluene; water / 95 °C

10.1: trifluoroacetic acid / chloroform / 36 °C

11.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; ammonium chloride / dichloromethane

12.1: Lawessons reagent / tetrahydrofuran / Reflux

13.1: mercury dichloride / acetonitrile / Reflux

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; Lawessons reagent; hydrogenchloride; methanol; titanium(IV) tetraethanolate; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; phosphorus pentachloride; isopropylmagnesium bromide; sodium methylate; potassium carbonate; ammonium chloride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; mercury dichloride; In tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; dichloromethane; chloroform; water; toluene; acetonitrile; butan-1-ol; 1.1: |Suzuki Coupling / 3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 9.1: |Suzuki Coupling;
DOI:10.1021/ml4001485

Reference yield:

: 1448631-44-4
C₂₄H₂₅ClN₂O₃S

: 1380088-44-7
(6S)-6-((1H-imidazol-2-yl)methyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepine

Guidance literature:: Multi-step reaction with 4 steps

1: trifluoroacetic acid / chloroform / 36 °C

2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; ammonium chloride / dichloromethane

3: Lawessons reagent / tetrahydrofuran / Reflux

4: mercury dichloride / acetonitrile / Reflux

With Lawessons reagent; ammonium chloride; triethylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; mercury dichloride; In tetrahydrofuran; dichloromethane; chloroform; acetonitrile;
DOI:10.1021/ml4001485