8-Fluoro-9-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-1,6-dioxo-2,3-dihydro-1H,6H-1λ⁴-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester

Base Information

• Chemical Name: 8-Fluoro-9-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-1,6-dioxo-2,3-dihydro-1H,6H-1λ⁴-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester
• CAS No.: 151295-35-1
• Molecular Formula: C₂₅H₂₅F₂N₃O₄S
• Molecular Weight: 501.554

Synonyms:8-Fluoro-9-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-1,6-dioxo-2,3-dihydro-1H,6H-1λ⁴-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester

Chemical Property of 8-Fluoro-9-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-1,6-dioxo-2,3-dihydro-1H,6H-1λ⁴-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester

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Technology Process of 8-Fluoro-9-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-1,6-dioxo-2,3-dihydro-1H,6H-1λ⁴-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester

There total 6 articles about 8-Fluoro-9-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-1,6-dioxo-2,3-dihydro-1H,6H-1λ⁴-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester 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: 63.0%

1-(4-Fluorophenyl)piperazine (2252-63-3) + ethyl 10-chloro-9-fluoro-2-methyl-7-oxo-2,3-dihydro-7H-pyrido<1,2,3-de><1,4>benzothiazine-6-carboxylate 1-oxide (116176-53-5) → 8-Fluoro-9-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-1,6-dioxo-2,3-dihydro-1H,6H-1λ4-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester (151295-35-1)

Guidance literature:

In N,N-dimethyl-formamide; at 100 ℃; for 2h;

DOI:10.1021/jm00074a028

Reference yield:

2,4-difluoro-3-chloro-nitrobenzene (3847-58-3) → 8-Fluoro-9-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-1,6-dioxo-2,3-dihydro-1H,6H-1λ4-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester (151295-35-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / NaOH / H₂O; dimethylsulfoxide / 2 h / 80 °C

2: 61 percent / FeSO₄*7H₂O, NH₄OH / H₂O / 1.) 2 h, RT, 2.) 15 min, 50 deg C

3: 46 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

4: 2.) polyphosphoric acid / 1.) 150 deg C, 2 h, 2.) 160 deg C, 1 h

5: 60 percent / MCPBA / ethanol / 2 h / Ambient temperature

6: 63 percent / dimethylformamide / 2 h / 100 °C

With ammonium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; PPA; iron(II) sulfate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm00074a028

Reference yield:

8-chloro-7-fluoro-2-methyl-3,4-dihydro-2H-1,4-benzothiazine (116176-51-3) → 8-Fluoro-9-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-methyl-1,6-dioxo-2,3-dihydro-1H,6H-1λ4-thia-3a-aza-phenalene-5-carboxylic acid ethyl ester (151295-35-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) polyphosphoric acid / 1.) 150 deg C, 2 h, 2.) 160 deg C, 1 h

2: 60 percent / MCPBA / ethanol / 2 h / Ambient temperature

3: 63 percent / dimethylformamide / 2 h / 100 °C

With PPA; 3-chloro-benzenecarboperoxoic acid; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00074a028

upstream raw materials:

1-(4-Fluorophenyl)piperazine

ethyl 10-chloro-9-fluoro-2-methyl-7-oxo-2,3-dihydro-7H-pyrido<1,2,3-de><1,4>benzothiazine-6-carboxylate 1-oxide

2,4-difluoro-3-chloro-nitrobenzene

8-chloro-7-fluoro-2-methyl-3,4-dihydro-2H-1,4-benzothiazine

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