methyl 2-(2-acetamidopropanamido)-6-phenylfuro[3,2-b]pyrazine-7-carboxylate

Base Information

• Chemical Name: methyl 2-(2-acetamidopropanamido)-6-phenylfuro[3,2-b]pyrazine-7-carboxylate
• CAS No.: 1369514-59-9
• Molecular Formula: C₁₉H₁₈N₄O₅
• Molecular Weight: 382.376
• Mol file: 1369514-59-9.mol

Synonyms:methyl 2-(2-acetamidopropanamido)-6-phenylfuro[3,2-b]pyrazine-7-carboxylate

Chemical Property of methyl 2-(2-acetamidopropanamido)-6-phenylfuro[3,2-b]pyrazine-7-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-(2-acetamidopropanamido)-6-phenylfuro[3,2-b]pyrazine-7-carboxylate

There total 6 articles about methyl 2-(2-acetamidopropanamido)-6-phenylfuro[3,2-b]pyrazine-7-carboxylate 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: 61.0%

N-acetyl-D,L-alanineamide (15962-47-7,27395-26-2,64397-30-4,71806-49-0) + 2-chloro-6-phenyl-furo[2,3-b]pyrazine-7-carboxylic acid methyl ester (1369514-32-8) → methyl 2-(2-acetamidopropanamido)-6-phenylfuro[3,2-b]pyrazine-7-carboxylate (1369514-59-9)

Guidance literature:

With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; at 140 ℃; for 0.75h; Microwave irradiation;

DOI:10.1016/j.tet.2012.02.022

Reference yield:

phenylacetylene (536-74-3) → methyl 2-(2-acetamidopropanamido)-6-phenylfuro[3,2-b]pyrazine-7-carboxylate (1369514-59-9)

Guidance literature:

Multi-step reaction with 4 steps

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.25 h / 80 °C / Inert atmosphere; Microwave irradiation

2: iodine / dichloromethane / 0.25 h / 20 °C

3: bis(3-methyl-2,3-dihydro-benzothiazole-2-ylidene) palladium(II) diiodide; tetrabutylammomium bromide; triethylamine / N,N-dimethyl acetamide / 2 h / 80 °C / 6000.6 Torr

4: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 0.75 h / 140 °C / Microwave irradiation

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; bis(3-methyl-2,3-dihydro-benzothiazole-2-ylidene) palladium(II) diiodide; tetrabutylammomium bromide; iodine; palladium diacetate; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; 1: Sonogashira coupling / 4: Buchwald-Hartwig amidation;

DOI:10.1016/j.tet.2012.02.022

Reference yield:

C14H11ClN2O3 → methyl 2-(2-acetamidopropanamido)-6-phenylfuro[3,2-b]pyrazine-7-carboxylate (1369514-59-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium periodate / tetrahydrofuran; water / 7 h / 20 °C

2.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; water / tert-butyl alcohol / 1 h / 20 °C

2.2: pH 2

3.1: toluene-4-sulfonic acid / 125 °C / Microwave irradiation

4.1: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / tetrahydrofuran / 0.75 h / 140 °C / Microwave irradiation

With sodium chlorite; sodium periodate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; water; palladium diacetate; caesium carbonate; toluene-4-sulfonic acid; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tetrahydrofuran; water; tert-butyl alcohol; 4.1: Buchwald-Hartwig amidation;

DOI:10.1016/j.tet.2012.02.022

upstream raw materials:

N-acetyl-D,L-alanineamide

2-chloro-6-phenyl-furo[2,3-b]pyrazine-7-carboxylic acid methyl ester

2-chloro-6-phenyl-7-vinyl-furo[2,3-b]pyrazine

2-chloro-6-phenylfuro[3,2-b]pyrazine-7-carbaldehyde