ethyl 6-acetyl-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate

Base Information

• Chemical Name: ethyl 6-acetyl-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate
• CAS No.: 921091-23-8
• Molecular Formula: C₂₀H₂₂N₂O₄S
• Molecular Weight: 386.472

Synonyms:ethyl 6-acetyl-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate

Chemical Property of ethyl 6-acetyl-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate

Chemical Property:

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Technology Process of ethyl 6-acetyl-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate

There total 7 articles about ethyl 6-acetyl-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate 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: 29.0%

ethyl 2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate (1351512-20-3) + acetyl chloride (75-36-5) → ethyl 6-acetyl-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate (921091-23-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2011.09.109

Reference yield:

phenylacetic acid (103-82-2) → ethyl 6-acetyl-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate (921091-23-8)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / tetrahydrofuran / 1.5 h / Reflux

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 48 h

3: trifluoroacetic acid / dichloromethane / 0.5 h

4: N-ethyl-N,N-diisopropylamine / dichloromethane

With thionyl chloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2011.09.109

Reference yield:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → ethyl 6-acetyl-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate (921091-23-8)

Guidance literature:

Multi-step reaction with 4 steps

1: morpholine; sulfur / ethanol / 20 - 40 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 48 h

3: trifluoroacetic acid / dichloromethane / 0.5 h

4: N-ethyl-N,N-diisopropylamine / dichloromethane

With morpholine; sulfur; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In ethanol; dichloromethane; 1: Gewald reaction;

DOI:10.1016/j.bmcl.2011.09.109

upstream raw materials:

phenylacetic acid

6-tert-butyl 3-ethyl 2-(2-phenylacetamido)-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate

ethyl 2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate

acetyl chloride

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