N-(2-(2-bromoethyl)-4-hydroxyphenyl)-1-methyl-4-(1-methyl-4-butanamido pyrrole-2-carboxamido)pyrrole-2-carboxamide

Base Information

• Chemical Name: N-(2-(2-bromoethyl)-4-hydroxyphenyl)-1-methyl-4-(1-methyl-4-butanamido pyrrole-2-carboxamido)pyrrole-2-carboxamide
• CAS No.: 413576-98-4
• Molecular Formula: C₂₄H₂₈BrN₅O₄
• Molecular Weight: 530.421
• Mol file: 413576-98-4.mol

Synonyms:N-(2-(2-bromoethyl)-4-hydroxyphenyl)-1-methyl-4-(1-methyl-4-butanamido pyrrole-2-carboxamido)pyrrole-2-carboxamide

Chemical Property of N-(2-(2-bromoethyl)-4-hydroxyphenyl)-1-methyl-4-(1-methyl-4-butanamido pyrrole-2-carboxamido)pyrrole-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2-(2-bromoethyl)-4-hydroxyphenyl)-1-methyl-4-(1-methyl-4-butanamido pyrrole-2-carboxamido)pyrrole-2-carboxamide

There total 6 articles about N-(2-(2-bromoethyl)-4-hydroxyphenyl)-1-methyl-4-(1-methyl-4-butanamido pyrrole-2-carboxamido)pyrrole-2-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: 40.0%

4-(4-butanamido-1-methylpyrrole-2-carboxamido)-1-methylpyrrole-2-carboxylic acid (157116-53-5) + 2-(2-amino-4-hydroxyphenyl)ethyl bromide (413577-25-0) → N-(2-(2-bromoethyl)-4-hydroxyphenyl)-1-methyl-4-(1-methyl-4-butanamido pyrrole-2-carboxamido)pyrrole-2-carboxamide (413576-98-4)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmc.2004.08.051

Reference yield:

4-benzyloxy-2-nitrophenylacetic acid (6860-79-3) → N-(2-(2-bromoethyl)-4-hydroxyphenyl)-1-methyl-4-(1-methyl-4-butanamido pyrrole-2-carboxamido)pyrrole-2-carboxamide (413576-98-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / borane / tetrahydrofuran / 4 h / 20 °C

2: 92 percent / triphenylphosphine; CBr₄ / acetonitrile

3: 100 percent / H₂ / Pd/C / tetrahydrofuran / 20 °C / atmospheric pressure

4: 40 percent / EDCI / dimethylformamide / 20 °C

With carbon tetrabromide; borane; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2004.08.051

Reference yield:

diethyl <4-(benzyloxy)-2-nitrophenyl>malonate (112089-51-7) → N-(2-(2-bromoethyl)-4-hydroxyphenyl)-1-methyl-4-(1-methyl-4-butanamido pyrrole-2-carboxamido)pyrrole-2-carboxamide (413576-98-4)

Guidance literature:

Multi-step reaction with 6 steps

1: NaOH / ethanol / 3 h / Heating

2: 1.41 g / HCl / tetrahydrofuran; H₂O / 1 h / pH 1 / Heating

3: 95 percent / borane / tetrahydrofuran / 4 h / 20 °C

4: 92 percent / triphenylphosphine; CBr₄ / acetonitrile

5: 100 percent / H₂ / Pd/C / tetrahydrofuran / 20 °C / atmospheric pressure

6: 40 percent / EDCI / dimethylformamide / 20 °C

With hydrogenchloride; sodium hydroxide; carbon tetrabromide; borane; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2004.08.051

upstream raw materials:

4-(4-butanamido-1-methylpyrrole-2-carboxamido)-1-methylpyrrole-2-carboxylic acid

2-(2-amino-4-hydroxyphenyl)ethyl bromide

4-benzyloxy-2-nitrophenylacetic acid

diethyl <4-(benzyloxy)-2-nitrophenyl>malonate

Downstream raw materials:

N-[2-(2-bromoethyl)-O-(4-nitrobenzylcarbonato)phenyl]-1-methyl-4-(1-methyl-4-butanamidopyrrole-2-carboxamido)pyrrole-2-carboxamide

Refernces

• 1、 -. "Compositions and methods of the use thereof achiral analogues of CC-1065 and the duocarmycins". Page column 31. . Retrieved 2010/02/05.