Ceritinib dihydrochloride

Base Information

• Chemical Name: Ceritinib dihydrochloride
• CAS No.: 1380575-43-8
• Molecular Formula: C₂₈H₃₆ClN₅O₃S*(x)ClH
• Molecular Weight: 594.59608
• UNII: 08381UU98P
• Mol file: 1380575-43-8.mol

Synonyms:1380575-43-8;Ceritinib dihydrochloride;LDK378 dihydrochloride;Ceritinib 2hcl;LDK378 2HCl (Ceritinib);LDK-378 hydrochloride;08381UU98P;5-chloro-2-N-(5-methyl-4-piperidin-4-yl-2-propan-2-yloxyphenyl)-4-N-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine;dihydrochloride;LDK-378 dihydrochloride(Ceritinib dihydrochloride);LDK-378 dihydrochloride;LDK378 (dihydrochloride);2,4-Pyrimidinediamine, 5-chloro-N4-(2-((1-methylethyl)sulfonyl)phenyl)-N2-(5-methyl-2-(1-methylethoxy)-4-(4-piperidinyl)phenyl)-, hydrochloride (1:2);2,4-Pyrimidinediamine, 5-chloro-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-N2-[5-methyl-2-(1-methylethoxy)-4-(4-piperidinyl)phenyl]-, hydrochloride (1:2);5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine dihydrochloride;CS-1407;LDK378 2HCl;SCHEMBL9936675;UNII-08381UU98P;BCP10604;EX-A1563;HY-15656A;MFCD26142928;s4967;5-Chloro-n2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine 2HCl;AC-29712;AS-75253;F11840;LDK378 dihydrochloride, Ceritinib dihydrochloride;1190399-48-4;5-chloro-N2-[5-methyl-4-(piperidin-4-yl)-2-(propan-2-yloxy)phenyl]-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine dihydrochloride

Chemical Property of Ceritinib dihydrochloride

Chemical Property:

• PSA: 116.85000
• LogP: 8.87040
• Solubility.: ≥12.38 mg/mL in EtOH with ultrasonic; ≥13.7 mg/mL in H2O; ≥29.65 mg/mL in DMSO
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 629.176094
• Heavy Atom Count: 40
• Complexity: 835

Purity/Quality:

>95% ^*data from raw suppliers

LDK3782HCl(Ceritinib) 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1C2CCNCC2)OC(C)C)NC3=NC=C(C(=N3)NC4=CC=CC=C4S(=O)(=O)C(C)C)Cl.Cl.Cl

Technology Process of Ceritinib dihydrochloride

There total 14 articles about Ceritinib dihydrochloride 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:

5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(propane-2-sulfonyl)phenyl)pyrimidine-2,4-diamine dihydrochloride (1380575-43-8) → 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine hydrochloride (1380575-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / acetone; water / 20 - 55 °C / pH 12.0

2: hydrogenchloride / water / 20 °C / pH 1

With hydrogenchloride; sodium hydroxide; In water; acetone;

Reference yield:

5-chloro-N2-[2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl]-N4-[2-(isopropylsulfonyl)phenyl]pyrimidine-2,4-diamine dihydrochloride (1190399-91-7) → 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine hydrochloride (1380575-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-dimethyl-formamide; isopropyl alcohol / 75 - 77 °C / Large scale

2: sodium hydroxide / acetone; water / 20 - 55 °C / pH 12.0

3: hydrogenchloride / water / 20 °C / pH 1

With hydrogenchloride; sodium hydroxide; In water; N,N-dimethyl-formamide; isopropyl alcohol; acetone;

Reference yield:

N,N-dibenzyl-4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-2-isopropoxy-5-methylaniline → 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(propane-2-sulfonyl)phenyl)pyrimidine-2,4-diamine dihydrochloride (1380575-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen; palladium on activated charcoal / methanol / 72 h / 4137.29 Torr

2: hydrogenchloride / methanol / 0.17 h / 0 °C

3: isopropyl alcohol / 14 h / 85 °C

With hydrogenchloride; palladium on activated charcoal; hydrogen; In methanol; isopropyl alcohol;

upstream raw materials:

5-chloro-N²-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N⁴-((2-isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine

ortho-nitrofluorobenzene

2-bromo-4-fluorotoluene

1-bromo-5-fluoro-2-methyl-4-nitrobenzene

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF CERITINIB". . . Retrieved 2016/12/26.
• 2、 -. "Novel kinase inhibitors". . . Retrieved 2017/08/02.