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

Base Information

• Chemical Name: 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-5-isobutyryl-2-(4-trifluoroacetamidophenyl)-4-oxothieno[2,3-b]pyridine
• CAS No.: 903520-54-7
• Molecular Formula: C₃₅H₃₀F₅N₃O₃S
• Molecular Weight: 667.7

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

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

Chemical Property:

Purity/Quality:

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

There total 12 articles about 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-5-isobutyryl-2-(4-trifluoroacetamidophenyl)-4-oxothieno[2,3-b]pyridine 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: 75.0%

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) + isopropylmagnesium chloride (1068-55-9) → 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-5-isobutyryl-2-(4-trifluoroacetamidophenyl)-4-oxothieno[2,3-b]pyridine (903520-54-7)

Guidance literature:

In 1,4-dioxane; 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-5-isobutyryl-2-(4-trifluoroacetamidophenyl)-4-oxothieno[2,3-b]pyridine (903520-54-7)

Guidance literature:

Multi-step reaction with 8 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

8.1: 75 percent / dioxane / 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 1,4-dioxane; 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-5-isobutyryl-2-(4-trifluoroacetamidophenyl)-4-oxothieno[2,3-b]pyridine (903520-54-7)

Guidance literature:

Multi-step reaction with 9 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

9.1: 75 percent / dioxane / 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 1,4-dioxane; tetrachloromethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0512894

upstream raw materials:

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

isopropylmagnesium chloride

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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