( 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butylester )

Base Information

• Chemical Name: ( 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butylester )
• CAS No.: 475084-96-9
• Molecular Formula: C29H37N3O3
• Molecular Weight: 475.631
• Mol file: 475084-96-9.mol

Synonyms:( 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butylester );4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]-1-butanol;[4-[(5,6-Diphenylpyrazinyl)(1-methylethyl)amino]butoxy]acetic acid 1,1-dimethylethyl ester

Chemical Property of ( 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butylester )

Chemical Property:

• Appearance/Colour: yellow
• Boiling Point: 592.3±50.0 °C(Predicted)
• PKA: 2.40±0.10(Predicted)
• PSA: 64.55000
• Density: 1.090±0.06 g/cm3(Predicted)
• LogP: 6.16390

Purity/Quality:

99.5% ^*data from raw suppliers

2-{4-[N-(5,6-Diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}aceticacidtert-butylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-{4-[N-(5,6-Diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butyl ester is an impurity of Selexipag (S253150), an orally available, highly selective, long-acting prostacyclin (IP) receptor agonist prodrug. It is a potential drug for the treatment of various vascular disorders such as pulmonary arterial hypertension and arteriosclerosis obliterans.

Technology Process of ( 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butylester )

There total 13 articles about ( 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butylester ) 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: 100.0%

4-[N-(5,6-diphenylpyrazine-2-yl)-N-isopropylamino]-1-butanol (475086-75-0) + bromoacetic acid tert-butyl ester (5292-43-3) → 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butyl ester (475084-96-9)

Guidance literature:

With cetyltrimethylammonim bromide; sodium hydroxide; In water; toluene; at 5 ℃; for 5h; Reagent/catalyst; Solvent;

Reference yield:

2-chloro-5,6-diphenylpyrazine (41270-66-0) → 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butyl ester (475084-96-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: water; isopropyl alcohol / 24 h / 150 °C / 10343.2 - 20686.5 Torr / Autoclave

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.58 h / 80 °C

2.2: 15 - 20 °C

3.1: sodium hydroxide; tetrabutylammomium bromide / water; toluene / 5 - 30 °C

With tetrabutylammomium bromide; sodium hydride; sodium hydroxide; In water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; mineral oil;

Reference yield:

4-isopropylamino-butyric acid ethyl ester → 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butyl ester (475084-96-9)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / -10 - 0 °C / Inert atmosphere

2: 2 h / 185 - 190 °C

3: sodium hydroxide; tetrabutylammomium bromide / water; toluene / 5 - 30 °C

With lithium aluminium tetrahydride; tetrabutylammomium bromide; sodium hydroxide; In tetrahydrofuran; water; toluene;

upstream raw materials:

4-[N-(5,6-diphenylpyrazine-2-yl)-N-isopropylamino]-1-butanol

bromoacetic acid tert-butyl ester

2-chloro-5,6-diphenylpyrazine

5,6-diphenyl-2-hydroxypyrazine

Downstream raw materials:

Selexipag

1-bromo-4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butane

MRE-269