N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine

Base Information

• Chemical Name: N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine
• CAS No.: 1097917-15-1
• Molecular Formula: C29H40N8O3S
• Molecular Weight: 580.754
• Mol file: 1097917-15-1.mol

Synonyms:N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine;

Chemical Property of N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine

Chemical Property:

• Boiling Point: 794.3±70.0 °C(Predicted)
• PKA: 8.14±0.42(Predicted)
• PSA: 127.43000
• Density: 1.276
• LogP: 4.28220
• Solubility.: insoluble in H2O; ≥14.53 mg/mL in DMSO; ≥4.9 mg/mL in EtOH with gentle warming and ultrasonic

Purity/Quality:

99% ^*data from raw suppliers

ASP 3026 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: ASP3026 is an ATP-competitive, second-generation ALK inhibitor (IC50 = 3.5 nM) that also inhibits ROS (IC50 = 8.9 nM) and ACK (IC50 = 5.8 nM). It inhibits neuroblastoma-activating ALK mutants F1174L (IC50 = 10 nM) and R1275Q (IC50 = 5.4 nM) and demonstrates antitumor activity in xenograft mouse models. ASP3026 has been shown to overcome crizotinib resistance in non-small cell lung cancer, and is currently being evaluated in clinical trials of patients with ALK-positive solid tumors.
• Uses: ASP3026 is a novel and selective anaplastic lymphoma kinase (ALK) inhibitor that shows potent anti-tumor activities. ASP3026 also shows potential efficacy for non-small cell lung cancer (NSCLC) and is expected to improve the therapeutic outcomes of patients with cancer with ALK abnormality. Potent ALK inhibitor.

Technology Process of N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine

There total 20 articles about N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine 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: 88.0%

1-methyl-piperazine (109-01-3) + 1-[3-methoxy-4-({4-[2-(propane-2-sulfonyl)anilino]-1,3,5-triazin-2-yl}amino)phenyl]piperidin-4-one (1097917-68-4) → N-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)-piperidin-1-yl]phenyl}-N′-[2-(propane-2-sulfonyl)phenyl]-1,3,5-triazine-2,4-diamine (1097917-15-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 40 ℃; for 7h; under 1861.76 Torr; Concentration; Reagent/catalyst; Solvent; Temperature; Time;

Reference yield: 57.0%

2-methoxy-4-[4-(4-methylpiperazin-1-yl)-piperidin-1-yl]-phenylamine + 4-chloro-N-[2-(propane-2-sulfonyl)phenyl]-1,3,5-triazin-2-amine (1097920-74-5) → N-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)-piperidin-1-yl]phenyl}-N′-[2-(propane-2-sulfonyl)phenyl]-1,3,5-triazine-2,4-diamine (1097917-15-1)

Guidance literature:

2-methoxy-4-[4-(4-methylpiperazin-1-yl)-piperidin-1-yl]-phenylamine; With methanesulfonic acid; In ethanol; at 20 ℃; for 0.25h;

4-chloro-N-[2-(propane-2-sulfonyl)phenyl]-1,3,5-triazin-2-amine; In ethanol; at 100 ℃; for 2h;

DOI:10.1248/cpb.c17-00784

Reference yield: 50.1%

2-methoxy-4-[4-(4-methylpiperazin-1-yl)-piperidin-1-yl]-phenylamine + 1-(1-(3-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine (761440-65-7) → N-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)-piperidin-1-yl]phenyl}-N′-[2-(propane-2-sulfonyl)phenyl]-1,3,5-triazine-2,4-diamine (1097917-15-1)

Guidance literature:

2-methoxy-4-[4-(4-methylpiperazin-1-yl)-piperidin-1-yl]-phenylamine; With methanesulfonic acid; In ethanol; at 20 ℃; for 0.25h;

1-[1-(3-methoxy-4-nitrophenyl)piperidin-4-yl]-4-methylpiperazine; In ethanol; at 100 ℃; for 5h;

upstream raw materials:

1-methyl-piperazine

1-[3-methoxy-4-({4-[2-(propane-2-sulfonyl)anilino]-1,3,5-triazin-2-yl}amino)phenyl]piperidin-4-one

1-(1-(3-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

4-chloro-N-[2-(propane-2-sulfonyl)phenyl]-1,3,5-triazin-2-amine

Downstream raw materials:

2-[(4-{[2-(isopropylsulfonyl)phenyl]amino}-1,3,5-triazin-2-yl)amino]-5-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenol

Refernces

• 1、 Iikubo, Kazuhiko,Kondoh, Yutaka,Shimada, Itsuro,Matsuya, Takahiro,Mori, Kenichi,Ueno, Yoko,Okada, Minoru. "Discovery of N-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}-N′-[2-(propane-2-sulfonyl)phenyl]-1,3,5-triazine-2,4-diamine (ASP3026), a potent and selective anaplastic lymphoma kinase (ALK) inhibitor". . p. 251 - 262. Retrieved 2018/03/13.
• 2、 -. "DI(ARYLAMINO)ARYL COMPOUND". Page/Page column 56; 76. . Retrieved 2010/04/25.