(R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid

Base Information

• Chemical Name: (R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid
• CAS No.: 1384512-98-4
• Molecular Formula: C₄₇H₅₀ClN₇O₆S₂
• Molecular Weight: 908.542

Synonyms:(R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid

Chemical Property of (R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid

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Technology Process of (R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid

There total 9 articles about (R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid 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:

ethyl 2-(3-iodobenzylidene)-3-oxobutanoate → (R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid (1384512-98-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine / 70 °C / Inert atmosphere

2: methanol / Inert atmosphere

3: sodium hydroxide / 1,4-dioxane; ethanol; water / Reflux; Inert atmosphere

4: copper(l) iodide; potassium carbonate; L-proline / dimethyl sulfoxide / 80 °C / Inert atmosphere

5: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.5 h / 20 °C / Inert atmosphere

6: pyridine / 0.5 h / 0 °C / Inert atmosphere

7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / Inert atmosphere

With pyridine; copper(l) iodide; palladium 10% on activated carbon; hydrogen; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; L-proline; sodium hydroxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 2: Paal-Knorr pyrrole synthesis;

DOI:10.1021/jm300608w

Reference yield:

m-iodobenzaldehyde (696-41-3) → (R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid (1384512-98-4)

Guidance literature:

Multi-step reaction with 8 steps

1: piperidine; acetic acid / toluene / Inert atmosphere; Reflux

2: 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine / 70 °C / Inert atmosphere

3: acetic acid / methanol / 24 h / 65 °C / Inert atmosphere; Sealed tube

4: sodium hydroxide / 1,4-dioxane; ethanol; water / Reflux; Inert atmosphere

5: copper(l) iodide; potassium carbonate; L-proline / dimethyl sulfoxide / 80 °C / Inert atmosphere

6: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.5 h / 20 °C / Inert atmosphere

7: pyridine / 0.5 h / 0 °C / Inert atmosphere

8: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / Inert atmosphere

With piperidine; pyridine; copper(l) iodide; palladium 10% on activated carbon; hydrogen; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; L-proline; sodium hydroxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 3: Paal-Knorr pyrrole synthesis;

DOI:10.1021/jm300608w

Reference yield:

ethyl 2-acetyl-4-(4-chlorophenyl)-3-(3-iodophenyl)-4-oxobutanoate (1384513-05-6) → (R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid (1384512-98-4)

Guidance literature:

Multi-step reaction with 6 steps

1: acetic acid / methanol / 24 h / 65 °C / Inert atmosphere; Sealed tube

2: sodium hydroxide / 1,4-dioxane; ethanol; water / Reflux; Inert atmosphere

3: copper(l) iodide; potassium carbonate; L-proline / dimethyl sulfoxide / 80 °C / Inert atmosphere

4: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.5 h / 20 °C / Inert atmosphere

5: pyridine / 0.5 h / 0 °C / Inert atmosphere

6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / Inert atmosphere

With pyridine; copper(l) iodide; palladium 10% on activated carbon; hydrogen; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; L-proline; sodium hydroxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Paal-Knorr pyrrole synthesis;

DOI:10.1021/jm300608w

upstream raw materials:

5-(4-chlorophenyl)-1,2-dimethyl-4-(3-(4-(4-nitrophenyl)-piperazin-1-yl)phenyl)-1H-pyrrole-3-carboxylic acid

ethyl 5-(4-chlorophenyl)-4-(3-iodophenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylate

ethyl 2-acetyl-4-(4-chlorophenyl)-3-(3-iodophenyl)-4-oxobutanoate

ethyl 5-(4-chlorophenyl)-4-(3-iodophenyl)-1-isopropyl-2-methyl-1H-pyrrole-3-carboxylate

Downstream raw materials:

(R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-1,2-dimethyl-N-(3-(4-methylpiperazin-1-yl)propyl)-1H-pyrrole-3-carboxamide

(R)-N-(4-(4-(3-(2-(4-chlorophenyl)-1,5-dimethyl-1H-pyrrol-3-yl)phenyl)piperazin-1-yl)phenyl)-4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrobenzenesulfonamide

(R)-5-(4-chlorophenyl)-4-(3-(4-(4-(4-((4-(dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrophenylsulfonamido)-phenyl)piperazin-1-yl)phenyl)-N,1,2-trimethyl-1H-pyrrole-3-carboxamide

C₅₁H₅₇ClN₈O₆S₂

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