3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-carboxamide

Base Information

• Chemical Name: 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-carboxamide
• CAS No.: 192886-69-4
• Molecular Formula: C₃₄H₂₉F₅N₄O₄S
• Molecular Weight: 684.687

Synonyms:3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-carboxamide

Chemical Property of 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-carboxamide

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SDS file from LookChem

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Technology Process of 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-carboxamide

There total 11 articles about 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-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: 94.0%

3-(N-benzyl-N-methylaminomethyl)-4,7-dihydro-7-(2,6-difluorobenzyl)-2-(4-trifluoroacetylaminophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylic acid ethyl ester (192886-68-3) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-carboxamide (192886-69-4)

Guidance literature:

N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; at 0 ℃;

3-(N-benzyl-N-methylaminomethyl)-4,7-dihydro-7-(2,6-difluorobenzyl)-2-(4-trifluoroacetylaminophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylic acid ethyl ester; In hexane; dichloromethane; at 0 ℃;

DOI:10.1021/jm0512894

Reference yield:

2,6-difluorobenzyl chloride (697-73-4) → 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-carboxamide (192886-69-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / K₂CO₃; KI / dimethylformamide / 20 - 50 °C

2.1: 71 percent / NaNO₃; H₂SO₄ / 0 °C

3.1: N-bromosuccinimide; 2,2'-azobis(isobutyronitrile) / CCl₄ / Heating

4.1: N,N-diisopropylethylamine / dimethylformamide / 20 °C

5.1: 96 percent / aq. HCl; Fe / ethanol / 0 °C

6.1: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

7.1: Me₃Al; N,N-diisopropylethylamine / CH₂Cl₂; hexane / 0 °C

7.2: 94 percent / CH₂Cl₂; hexane / 0 °C

With hydrogenchloride; sodium nitrate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sulfuric acid; trimethylaluminum; iron; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; potassium iodide; In tetrachloromethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0512894

Reference yield:

ethyl N-[3-carboxy-4-methyl-5-phenyl-2-thienyl]aminomethylenemalonate (174072-77-6) → 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-carboxamide (192886-69-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 60 percent / polyphosphate ester / 120 °C

2.1: 90 percent / K₂CO₃; KI / dimethylformamide / 20 - 50 °C

3.1: 71 percent / NaNO₃; H₂SO₄ / 0 °C

4.1: N-bromosuccinimide; 2,2'-azobis(isobutyronitrile) / CCl₄ / Heating

5.1: N,N-diisopropylethylamine / dimethylformamide / 20 °C

6.1: 96 percent / aq. HCl; Fe / ethanol / 0 °C

7.1: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

8.1: Me₃Al; N,N-diisopropylethylamine / CH₂Cl₂; hexane / 0 °C

8.2: 94 percent / CH₂Cl₂; hexane / 0 °C

With hydrogenchloride; sodium nitrate; N-Bromosuccinimide; polyphosphate ester; 2,2'-azobis(isobutyronitrile); sulfuric acid; trimethylaluminum; iron; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; potassium iodide; In tetrachloromethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0512894

upstream raw materials:

3-(N-benzyl-N-methylaminomethyl)-4,7-dihydro-7-(2,6-difluorobenzyl)-2-(4-trifluoroacetylaminophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

N,O-dimethylhydroxylamine*hydrochloride

ethyl N-[3-carboxy-4-methyl-5-phenyl-2-thienyl]aminomethylenemalonate

2-[(3-ethoxycarbonyl-4-methyl-5-phenyl-thiophen-2-ylamino)-methylene]-malonic acid diethyl ester

Downstream raw materials:

({4-[3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridin-2-yl]-phenylcarbamoyl}-methyl)-carbamic acid tert-butyl ester

acetic acid 1-{4-[3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridin-2-yl]-phenylcarbamoyl}-cyclopropyl ester

acetic acid 1-{4-[3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridin-2-yl]-phenylcarbamoyl}-1-methyl-ethyl ester

2-(4-aminophenyl)-3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-5-isobutyryl-4-oxothieno[2,3-b]pyridine

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