2-((6S)-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-((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide
• CAS No.: 1380088-19-6
• Molecular Formula: C₂₂H₂₂ClN₃O₂S
• Molecular Weight: 427.955
• Mol file: 1380088-19-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 2-((6S)-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:

2-((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)acetic acid (1380088-18-5) + ethylamine (75-04-7,85404-22-4) → 2-((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide (1380088-19-6)

Guidance literature:

With base; coupling reagent; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/ml4001485

Reference yield:

C24H25ClN2O3S (1448631-44-4) → 2-((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide (1380088-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / chloroform / 36 °C

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

With trifluoroacetic acid; In chloroform; N,N-dimethyl-formamide;

DOI:10.1021/ml4001485

Reference yield:

methyl 2-bromo-4,5-dimethylthiophene-3-carboxylate (1019115-42-4) → 2-((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)-N-ethylacetamide (1380088-19-6)

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; 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: 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; diethyl ether; 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

upstream raw materials:

C₂₄H₂₅ClN₂O₃S

methyl 2-bromo-4,5-dimethylthiophene-3-carboxylate

(3-methylisoxazol-5-yl)methyl acetate

methyl 4,5-dimethylthiophene-3-carboxylate