2-((6R)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide

Base Information

Chemical Name:2-((6R)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide
CAS No.:1380088-23-2
Molecular Formula:C₂₂H₂₂ClN₃O₂S
Molecular Weight:427.955
Hs Code.:

Synonyms:2-((6R)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide

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Chemical Property of 2-((6R)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide

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Technology Process of 2-((6R)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide

There total 13 articles about 2-((6R)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide 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:

: 1380088-21-0
2-((6R)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)acetic acid

: 75-04-7,85404-22-4
ethylamine

: 1380088-23-2
2-((6R)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide

Guidance literature:: With base; coupling reagent; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1021/ml4001485

Reference yield:

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

: 1380088-23-2
2-((6R)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide

Guidance literature:: Multi-step reaction with 11 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 / 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: base; coupling reagent / N,N-dimethyl-formamide / 0 - 20 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; 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; dimethyl sulfoxide; trifluoroacetic acid; In tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; 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:

: 14559-13-8
methyl 4,5-dimethylthiophene-3-carboxylate

: 1380088-23-2
2-((6R)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide

Guidance literature:: Multi-step reaction with 12 steps

1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / 20 °C

2.1: 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

3.1: sodium methylate; methanol / 1.5 h

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

4.2: -78 - 20 °C

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

6.1: 1-methyl-pyrrolidin-2-one / 6.17 h / -8.5 - 5 °C

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

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

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

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

11.1: trifluoroacetic acid / chloroform / 36 °C

12.1: base; coupling reagent / N,N-dimethyl-formamide / 0 - 20 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; methanol; titanium(IV) tetraethanolate; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; phosphorus pentachloride; isopropylmagnesium bromide; sodium methylate; potassium carbonate; dimethyl sulfoxide; trifluoroacetic acid; In tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; butan-1-ol; 2.1: |Suzuki Coupling / 4.1: |Swern Oxidation / 4.2: |Swern Oxidation / 10.1: |Suzuki Coupling;
DOI:10.1021/ml4001485