3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide

Base Information

• Chemical Name: 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide
• CAS No.: 871656-70-1
• Molecular Formula: C₂₃H₂₅N₃O₄
• Molecular Weight: 407.469
• Mol file: 871656-70-1.mol

Synonyms:3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide

Chemical Property of 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide

There total 7 articles about 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide 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: 81.0%

5-methylpyrazin-2-amine (5521-58-4) + 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(phenylmethyl)oxy]benzoic acid (851885-41-1) → 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide (871656-70-1)

Guidance literature:

3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(phenylmethyl)oxy]benzoic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

5-methylpyrazin-2-amine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/acs.oprd.8b00175

Reference yield:

5-methylpyrazin-2-amine (5521-58-4) + C18H19ClO4 → 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide (871656-70-1)

Guidance literature:

With pyridine; In dichloromethane; at 5 - 20 ℃; for 18h;

Reference yield:

methyl 3-(benzyloxy)-5-hydroxybenzoate (54915-31-0) → 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide (871656-70-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran

2.1: sodium hydroxide / methanol

3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane

3.2: 0 - 20 °C

With oxalyl dichloride; di-isopropyl azodicarboxylate; N,N-dimethyl-formamide; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 1.1: |Mitsunobu Displacement;

DOI:10.1021/acs.oprd.8b00175

upstream raw materials:

5-methylpyrazin-2-amine

3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(phenylmethyl)oxy]benzoic acid

methyl 3-(benzyloxy)-5-hydroxybenzoate

methyl 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(phenylmethyl)oxy]benzoate

Downstream raw materials:

3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

AZD₁₆₅₆

3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoic acid