6-(Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-1-(1-naphthalenylsulfonyl)-1H-indoledihydrochloride

Base Information

• Chemical Name: 6-(Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-1-(1-naphthalenylsulfonyl)-1H-indoledihydrochloride
• CAS No.: 299433-10-6
• Molecular Formula: C₂₅H₂₅N₃O₂S
• Molecular Weight: 431.558
• Mol file: 299433-10-6.mol

Synonyms:6-(Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-1-(1-naphthalenylsulfonyl)-1H-indoledihydrochloride;NPS ALX Compound 4a dihydrochloride

Chemical Property of 6-(Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-1-(1-naphthalenylsulfonyl)-1H-indoledihydrochloride

Chemical Property:

• Boiling Point: 662.2±65.0 °C(Predicted)
• PKA: 8.65±0.20(Predicted)
• PSA: 53.93000
• Density: 1.36±0.1 g/cm3(Predicted)
• LogP: 7.00360
• Storage Temp.: Store at +4°C

Purity/Quality:

≥99% by HPLC ^*data from raw suppliers

NPS ALX Compound 4a dihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: NPS ALX Compound 4a dihydrochloride is a competitive SR-6 antagonist.

Technology Process of 6-(Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-1-(1-naphthalenylsulfonyl)-1H-indoledihydrochloride

There total 4 articles about 6-(Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-1-(1-naphthalenylsulfonyl)-1H-indoledihydrochloride 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: 70.0%

1-Naphthalenesulfonyl chloride (85-46-1) + 2-(1H-indol-6-yl)-octahydropyrrolo[1,2-a]pyrazine (299433-01-5) → 2-(1-(naphthalen-1-ylsulfonyl)-1H-indol-6-yl)octahydropyrrolo[1,2-a]pyrazine (299433-10-6)

Guidance literature:

2-(1H-indol-6-yl)-octahydropyrrolo[1,2-a]pyrazine; With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 0.25h;

1-Naphthalenesulfonyl chloride; In tetrahydrofuran;

Reference yield:

6-bromo-1H-indole (52415-29-9) → 2-(1-(naphthalen-1-ylsulfonyl)-1H-indol-6-yl)octahydropyrrolo[1,2-a]pyrazine (299433-10-6)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 0 °C

2: NaOt-Bu; Pd(OAc)2; t-Bu₃P / xylene / 120 °C

3: TBAF / tetrahydrofuran

4: NaHMDS / tetrahydrofuran

With palladium diacetate; tri-tert-butyl phosphine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; sodium t-butanolate; In tetrahydrofuran; N,N-dimethyl-formamide; xylene; 1: silylation / 2: Condensation / 3: desilylation / 4: sulfonylation;

DOI:10.1016/S0960-894X(00)00320-6

Reference yield:

6-bromo-1-(triisopropylsilyl)-1H-indole (299432-99-8) → 2-(1-(naphthalen-1-ylsulfonyl)-1H-indol-6-yl)octahydropyrrolo[1,2-a]pyrazine (299433-10-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOt-Bu; Pd(OAc)2; t-Bu₃P / xylene / 120 °C

2: TBAF / tetrahydrofuran

3: NaHMDS / tetrahydrofuran

With palladium diacetate; tri-tert-butyl phosphine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium t-butanolate; In tetrahydrofuran; xylene; 1: Condensation / 2: desilylation / 3: sulfonylation;

DOI:10.1016/S0960-894X(00)00320-6

upstream raw materials:

1-Naphthalenesulfonyl chloride

2-(1H-indol-6-yl)-octahydropyrrolo[1,2-a]pyrazine

6-bromo-1H-indole

6-bromo-1-(triisopropylsilyl)-1H-indole

Refernces

• 1、 Isaac, Methvin,Slassi, Abdelmalik,Xin, Tao,MacLean, Neil,Wilson, Julie,McCallum, Kirk,Wang, Hong,Demchyshyn, Lidia. "6-bicyclopiperazinyl-1-arylsulfonylindoles and 6-bicyclopiperidinyl-1-arylsulfonylindoles derivatives as novel, potent, and selective 5-HT6 receptor antagonists". . p. 1719 - 1721. Retrieved 2007/10/03.