ABT-639

Base Information

• Chemical Name: ABT-639
• CAS No.: 1235560-28-7
• Molecular Formula: C₂₀H₂₀ClF₂N₃O₃S
• Molecular Weight: 455.913
• Mol file: 1235560-28-7.mol

Synonyms:ABT-639

Chemical Property of ABT-639

Chemical Property:

• Boiling Point: 612.2±65.0 °C(Predicted)
• PKA: 6.80±0.10(Predicted)
• Density: 1.51±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

ABT639 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: ABT-639 is a selective T-type calcium channel blocker with efficacy in a wide range of preclinical models of nociceptive and neuropathic pain.ABT-639 produces robust antinociceptive activity in experimental pain models at doses that do not significantly alter psychomotor or hemodynamic function in the rat. ABT-639 is a T-type calcium channel blocker. It inhibits inactivated-state Cav3.2 channels with an IC50 value of 2.3 μM and inactivated-state Cav3.1 and Cav3.3 channels by 50 and 39%, respectively, when used at a concentration of 10 μM. ABT-639 selectively inhibits inactivated-state T-type calcium currents over resting-state currents in rat dorsal root ganglion (DRG) neurons (IC50s = 7.6 and >30 μM, respectively). It reverses the hind limb grip force deficit in a rat model of osteoarthritic pain induced by monoiodoacetic acid (MIA; ED50 = 2 mg/kg). ABT-639 also increases the paw withdrawal threshold in rat spinal nerve ligation (SNL) and chronic constriction injury (CCI) models of neuropathic pain in a dose-dependent manner and attenuates cold allodynia in the CCI rat model when administered at doses greater than or equal to 3 mg/kg.

Technology Process of ABT-639

There total 4 articles about ABT-639 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:

2-chloro-4-fluoro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid (1235560-30-1) + (8aR)-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine (96193-27-0) → ABT-639 (1235560-28-7)

Guidance literature:

2-chloro-4-fluoro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid; (8aR)-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine; With HATU; In 2-methyltetrahydrofuran; ISOPROPYLAMIDE; at 20 ℃;

With sodium hydrogencarbonate; In 2-methyltetrahydrofuran; ISOPROPYLAMIDE;

Reference yield:

2-Fluoroaniline (348-54-9) + (R)-4-chloro-2-fluoro-5-(octahydropyrrolo[1,2-a]pyrazine-2-carbonyl)benzene-1-sulfonyl chloride → ABT-639 (1235560-28-7)

Guidance literature:

2-Fluoroaniline; (R)-4-chloro-2-fluoro-5-(octahydropyrrolo[1,2-a]pyrazine-2-carbonyl)benzene-1-sulfonyl chloride; In dichloromethane; at 20 ℃;

With sodium carbonate; In methanol; dichloromethane; for 0.5h;

DOI:10.1021/acsmedchemlett.5b00023

Reference yield:

2-chloro-5-(chlorosulfonyl)-4-fluorobenzoic acid (264927-50-6) → ABT-639 (1235560-28-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C

2.1: dichloromethane / 1 h / 20 °C

2.2: 20 °C

3.1: dichloromethane / 20 °C

3.2: 0.5 h

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1021/acsmedchemlett.5b00023

upstream raw materials:

2-chloro-4-fluoro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid

(8aR)-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine

2-chloro-5-(chlorosulfonyl)-4-fluorobenzoic acid

2-chloro-5-( chlorosulfonyl)-4-fluorobenzoyl chloride

Downstream raw materials:

4-chloro-2-fluoro-N-(2-fluorophenyl)-5-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide hydrochloride