N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide

Base Information

• Chemical Name: N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide
• CAS No.: 1513879-19-0
• Molecular Formula: C₂₂H₁₈ClN₅O₂
• Molecular Weight: 419.87
• Mol file: 1513879-19-0.mol

Synonyms:N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide

Chemical Property of N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide

Chemical Property:

• Density: 1.35±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

KDU691 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: KDU691 is an antimalarial compound. It inhibits recombinant P. vivax phosphatidylinositol 4-kinase (PI4K) with an IC50 value of 1.5 nM. KDU691 is selective for P. vivax PI4K over recombinant human PI4KβIII and PI3Kα, -β, -γ, and -δ (IC50s = 7.9, 8.8, 2.4, 8, and 3.4 μM, respectively), as well as VPS34 (IC50 = >9.7 μM) and 36 additional kinases in a panel of lipid and protein kinases (IC50s = >10 μM). It is active against P. falciparum and P. yoelii schizonts (IC50s = 0.06 and 0.04 μM, respectively), as well as P. cynomolgi schizonts and hypnozoites (IC50s = 0.11 and 0.2 μM, respectively). KDU691 completely prevents, but does not eradicate established, P. cynomolgi infection in rhesus monkeys when administered at a dose of 20 mg/kg.
• Uses: KDU691, is a PI4K inhibitor.

Technology Process of N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide

There total 6 articles about N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-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: 80.2%

[4-(methylcarbamoyl)phenyl]boronic acid + 3-bromo-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (1607830-47-6) → N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide (1513879-19-0)

Guidance literature:

With potassium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; 1,2-dimethoxyethane; water; at 110 ℃; for 0.5h; Microwave irradiation;

DOI:10.1021/ml500244m

Reference yield:

ethyl 5-aminopyrazine-2-carboxylate (54013-06-8) → N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide (1513879-19-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydrogencarbonate / water; ethanol / 16 h / 90 °C

2.1: N-Bromosuccinimide / dichloromethane / 3 h / 20 °C

3.1: sodium hydroxide / tetrahydrofuran; water / 1.5 h / 60 °C

4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C

4.2: 3 h / 20 °C

5.1: dipotassium hydrogenphosphate / tetrahydrofuran; water / 0.75 h / 150 °C / Microwave irradiation

With dipotassium hydrogenphosphate; N-Bromosuccinimide; oxalyl dichloride; sodium hydrogencarbonate; N,N-dimethyl-formamide; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; 5.1: |Suzuki Coupling;

Reference yield:

ethyl pyrrolo[1,2-a]pyrazine-3-carboxylate (588720-67-6) → N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide (1513879-19-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide / dichloromethane / 3 h / 20 °C

2.1: sodium hydroxide / tetrahydrofuran; water / 1.5 h / 60 °C

3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C

3.2: 3 h / 20 °C

4.1: dipotassium hydrogenphosphate / tetrahydrofuran; water / 0.75 h / 150 °C / Microwave irradiation

With dipotassium hydrogenphosphate; N-Bromosuccinimide; oxalyl dichloride; N,N-dimethyl-formamide; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; 4.1: |Suzuki Coupling;

upstream raw materials:

ethyl 5-aminopyrazine-2-carboxylate

3-bromo-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide

ethyl pyrrolo[1,2-a]pyrazine-3-carboxylate

ethyl 3-bromoimidazo[1,2-a]pyrazine-6-carboxylate