4-(4-(3-(2-methylthiazol-4-yl)benzamido)phenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide

Base Information

• Chemical Name: 4-(4-(3-(2-methylthiazol-4-yl)benzamido)phenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide
• CAS No.: 1428305-91-2
• Molecular Formula: C₂₈H₃₁N₅O₂S
• Molecular Weight: 501.652
• Mol file: 1428305-91-2.mol

Synonyms:4-(4-(3-(2-methylthiazol-4-yl)benzamido)phenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide

Chemical Property of 4-(4-(3-(2-methylthiazol-4-yl)benzamido)phenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(4-(3-(2-methylthiazol-4-yl)benzamido)phenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide

There total 4 articles about 4-(4-(3-(2-methylthiazol-4-yl)benzamido)phenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-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: 79.0%

4-(4-aminophenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide (1187065-42-4) + 3-(2-methyl thiazol-4-yl)-benzoic acid (28077-41-0) → 4-(4-(3-(2-methylthiazol-4-yl)benzamido)phenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide (1428305-91-2)

Guidance literature:

4-(4-aminophenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide; With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at -5 ℃; for 0.25h; Inert atmosphere;

3-(2-methyl thiazol-4-yl)-benzoic acid; In N,N-dimethyl-formamide; for 3h; Inert atmosphere;

DOI:10.1021/jm301882a

Reference yield:

1-methyl-2-trichloroacetyl-1H-pyrrole (21898-65-7) → 4-(4-(3-(2-methylthiazol-4-yl)benzamido)phenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide (1428305-91-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide / tetrahydrofuran / 6 h / -10 - 20 °C

2.1: tetrahydrofuran / 20 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; toluene; water / 100 °C / Inert atmosphere; Microwave irradiation

4.1: N-ethyl-N,N-diisopropylamine; HATU; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 0.25 h / -5 °C / Inert atmosphere

4.2: 3 h / Inert atmosphere

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene; 3.1: |Suzuki Coupling;

DOI:10.1021/jm301882a

Reference yield:

1-(4-bromo-1-methyl-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one (184643-69-4) → 4-(4-(3-(2-methylthiazol-4-yl)benzamido)phenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide (1428305-91-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 20 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; toluene; water / 100 °C / Inert atmosphere; Microwave irradiation

3.1: N-ethyl-N,N-diisopropylamine; HATU; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 0.25 h / -5 °C / Inert atmosphere

3.2: 3 h / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene; 2.1: |Suzuki Coupling;

DOI:10.1021/jm301882a

upstream raw materials:

1-methyl-2-trichloroacetyl-1H-pyrrole

1-(4-bromo-1-methyl-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one

4-(4-aminophenyl)-N-(3-(dimethylamino)propyl)-1-methyl-1H-pyrrole-2-carboxamide

3-(2-methyl thiazol-4-yl)-benzoic acid