3-cyano-N-(3,4-dichlorobenzyl)-N-(2-(dimethylamino)ethyl)-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxamide

Base Information

• Chemical Name: 3-cyano-N-(3,4-dichlorobenzyl)-N-(2-(dimethylamino)ethyl)-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxamide
• CAS No.: 1450743-13-1
• Molecular Formula: C₂₅H₂₁Cl₂FN₄OS
• Molecular Weight: 515.438

Synonyms:3-cyano-N-(3,4-dichlorobenzyl)-N-(2-(dimethylamino)ethyl)-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxamide

Chemical Property of 3-cyano-N-(3,4-dichlorobenzyl)-N-(2-(dimethylamino)ethyl)-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxamide

Chemical Property:

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Technology Process of 3-cyano-N-(3,4-dichlorobenzyl)-N-(2-(dimethylamino)ethyl)-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxamide

There total 6 articles about 3-cyano-N-(3,4-dichlorobenzyl)-N-(2-(dimethylamino)ethyl)-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-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: 49.0%

3-bromo-N-(3,4-dichlorobenzyl)-N-(2-(dimethylamino)ethyl)-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxamide (1450743-08-4) + copper(l) cyanide → 3-cyano-N-(3,4-dichlorobenzyl)-N-(2-(dimethylamino)ethyl)-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxamide (1450743-13-1)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 20 - 220 ℃; for 0.75h; Microwave irradiation;

DOI:10.1016/j.bmc.2013.05.067

Reference yield:

4-Bromothiophen-2-aldehyde (18791-75-8) → 3-cyano-N-(3,4-dichlorobenzyl)-N-(2-(dimethylamino)ethyl)-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxamide (1450743-13-1)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium ethanolate / ethanol / 2.5 h / -10 - 20 °C

2: 5,5-dimethyl-1,3-cyclohexadiene / 2 h / 120 °C

3: copper diacetate; triethylamine; pyridine / 21 h / 20 °C / Molecular sieve

4: sodium hydroxide / tetrahydrofuran; ethanol / 2.5 h / 65 - 75 °C

5: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 30 h / 20 °C

6: 1-methyl-pyrrolidin-2-one / 0.75 h / 20 - 220 °C / Microwave irradiation

With pyridine; sodium ethanolate; copper diacetate; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; 5,5-dimethyl-1,3-cyclohexadiene; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2013.05.067

Reference yield:

ethyl 2-azido-3-(4-bromo-2-thienyl)acrylate (934246-45-4) → 3-cyano-N-(3,4-dichlorobenzyl)-N-(2-(dimethylamino)ethyl)-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxamide (1450743-13-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 5,5-dimethyl-1,3-cyclohexadiene / 2 h / 120 °C

2: copper diacetate; triethylamine; pyridine / 21 h / 20 °C / Molecular sieve

3: sodium hydroxide / tetrahydrofuran; ethanol / 2.5 h / 65 - 75 °C

4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 30 h / 20 °C

5: 1-methyl-pyrrolidin-2-one / 0.75 h / 20 - 220 °C / Microwave irradiation

With pyridine; copper diacetate; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; 5,5-dimethyl-1,3-cyclohexadiene; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2013.05.067

upstream raw materials:

4-Bromothiophen-2-aldehyde

ethyl 2-azido-3-(4-bromo-2-thienyl)acrylate

ethyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate

ethyl 3-bromo-4-(4-fluorophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

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