tert-butyl (N-tert-butoxycarbonyl)(5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-yl)carbamate

Base Information

• Chemical Name: tert-butyl (N-tert-butoxycarbonyl)(5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-yl)carbamate
• CAS No.: 1432790-84-5
• Molecular Formula: C₃₁H₃₆N₆O₆S
• Molecular Weight: 620.729
• Mol file: 1432790-84-5.mol

Synonyms:tert-butyl (N-tert-butoxycarbonyl)(5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-yl)carbamate

Chemical Property of tert-butyl (N-tert-butoxycarbonyl)(5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (N-tert-butoxycarbonyl)(5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-yl)carbamate

There total 3 articles about tert-butyl (N-tert-butoxycarbonyl)(5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-yl)carbamate 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%

tert-butyl N-(3-ethynyl-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)N-tertbutoxycarbonyl-carbamate ? (1232423-98-1) + Phenyl azide (622-37-7) → tert-butyl (N-tert-butoxycarbonyl)(5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-yl)carbamate (1432790-84-5)

Guidance literature:

With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In tert-butyl alcohol; at 20 - 40 ℃;

Reference yield:

tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate (1350351-56-2) → tert-butyl (N-tert-butoxycarbonyl)(5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-yl)carbamate (1432790-84-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate / methanol / 1 h / 20 °C

2: sodium L-ascorbate; copper(ll) sulfate pentahydrate / tert-butyl alcohol; water; tert-butyl methyl ether / 48 h / 20 - 40 °C

With copper(ll) sulfate pentahydrate; sodium carbonate; sodium L-ascorbate; In methanol; tert-butyl methyl ether; water; tert-butyl alcohol;

DOI:10.1021/acs.jmedchem.9b00426

Reference yield:

4-(isopropylsulfonyl)phenylboronic acid (850567-98-5) → tert-butyl (N-tert-butoxycarbonyl)(5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-yl)carbamate (1432790-84-5)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium phosphate; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / water; acetonitrile / 1 h / 60 °C

2: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

4: dmap; triethylamine / dichloromethane / 18 h / 20 °C

5: sodium carbonate / methanol / 1 h / 20 °C

6: sodium L-ascorbate; copper(ll) sulfate pentahydrate / tert-butyl alcohol; water; tert-butyl methyl ether / 48 h / 20 - 40 °C

With dmap; potassium phosphate; N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(ll) sulfate pentahydrate; bis(tri-t-butylphosphine)palladium⁽⁰⁾; sodium carbonate; sodium L-ascorbate; triethylamine; In methanol; dichloromethane; tert-butyl methyl ether; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1: |Suzuki Coupling / 3: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.jmedchem.9b00426

upstream raw materials:

tert-butyl N-(3-ethynyl-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)N-tertbutoxycarbonyl-carbamate ?

Phenyl azide

tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate

4-(isopropylsulfonyl)phenylboronic acid