5-amino-3-(4-fluorophenyl)-4-oxo-N-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxamide

Base Information

• Chemical Name: 5-amino-3-(4-fluorophenyl)-4-oxo-N-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxamide
• CAS No.: 1391029-78-9
• Molecular Formula: C₁₅H₁₀F₄N₄O₂S
• Molecular Weight: 386.33

Synonyms:5-amino-3-(4-fluorophenyl)-4-oxo-N-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxamide

Chemical Property of 5-amino-3-(4-fluorophenyl)-4-oxo-N-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxamide

Chemical Property:

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Technology Process of 5-amino-3-(4-fluorophenyl)-4-oxo-N-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxamide

There total 3 articles about 5-amino-3-(4-fluorophenyl)-4-oxo-N-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxamide 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: 54.0%

trifluoroethylamine (753-90-2) + 5-amino-3-(4-fluorophenyl)-4-oxo-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxylic acid (1282449-07-3) → 5-amino-3-(4-fluorophenyl)-4-oxo-N-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxamide (1391029-78-9)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 ℃; for 4h;

DOI:10.1016/j.bmc.2012.05.027

Reference yield:

ethyl 5-cyano-1-(4-fluorophenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate (443666-61-3) → 5-amino-3-(4-fluorophenyl)-4-oxo-N-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxamide (1391029-78-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: morpholine; sulfur / ethanol / 0.25 h / 150 °C / Microwave irradiation

2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 16 h / 20 °C

2.2: pH 2

3.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 4 h / 20 °C

With morpholine; sulfur; lithium hydroxide monohydrate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide; 1.1: Gewald reaction;

DOI:10.1016/j.bmc.2012.05.027

Reference yield:

4-fluoroaniline (371-40-4) → 5-amino-3-(4-fluorophenyl)-4-oxo-N-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxamide (1391029-78-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogenchloride; sodium nitrite / ethanol; water / 0 °C

1.2: 4 h / 0 °C

2.1: sodium acetate; acetic acid / 0.07 h / 170 °C / Microwave irradiation

3.1: morpholine; sulfur / ethanol / 0.25 h / 150 °C / Microwave irradiation

4.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 16 h / 20 °C

4.2: pH 2

5.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 4 h / 20 °C

With morpholine; hydrogenchloride; sulfur; lithium hydroxide monohydrate; sodium acetate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium nitrite; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide; 3.1: Gewald reaction;

DOI:10.1016/j.bmc.2012.05.027

upstream raw materials:

ethyl 5-cyano-1-(4-fluorophenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate

trifluoroethylamine

5-amino-3-(4-fluorophenyl)-4-oxo-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxylic acid

4-fluoroaniline

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