Volitinib

Base Information

• Chemical Name: Volitinib
• CAS No.: 1313725-88-0
• Molecular Formula: C17H15N9
• Molecular Weight: 345.36
• Mol file: 1313725-88-0.mol

Synonyms:Volitinib;Savolitinib;HMPL-504(AZD6094, Volitinib);AZD6094,Volitinib, HMPL-504, Savolitinib;1-[(1S)-1-Imidazo[1,2-a]pyridin-6-ylethyl]-6-(1-methyl-1H-pyrazol-4-yl)-1H-1,2,3-triazolo[4,5-b]pyrazine;(S)-1-(1-(imidazo[1,2-a]pyridin-6-yl)ethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine

Chemical Property of Volitinib

Chemical Property:

• PKA: 5.67±0.50(Predicted)
• PSA: 91.61000
• Density: 1.55±0.1 g/cm3(Predicted)
• LogP: 1.87880
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

Savolitinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Savolitinib is a potent and highly selective c-Met inhibitor. Savoltinib demonstrated anti-tumor efficacy in a panel of cMet-dysregulated gastric cancer PDX models. Savolitinib also demonstrated good antitmuor activities.

Technology Process of Volitinib

There total 18 articles about Volitinib 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: 76.0%

5-bromo-3-[(1S)-1-imidazo[1,2-a]pyridin-1-ium-6-ylethyl]triazolo[4,5-b]pyrazine chloride + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → savolitinib (1313725-88-0)

Guidance literature:

With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; iso-butanol; In water; at 65 ℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1021/acs.joc.8b02351

Reference yield:

(S)-6-bromo-1-(1-(imidazo[1,2-a]pyridin-6-yl)ethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine hydrochloride + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → savolitinib (1313725-88-0)

Guidance literature:

(S)-6-bromo-1-(1-(imidazo[1,2-a]pyridin-6-yl)ethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine hydrochloride; 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole; With potassium carbonate; In water; iso-butanol; for 0.0833333h; Inert atmosphere;

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium; In water; iso-butanol; at 30 - 65 ℃; for 2h; Inert atmosphere;

Reference yield:

(1S)-1-imidazo[1,2-a]pyridin-6-ylethanamine (1259603-82-1,1259780-63-6) → savolitinib (1313725-88-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine; 1-methyl-pyrrolidin-2-one / 50 h / 120 °C / Inert atmosphere

2.1: acetic acid; sodium nitrite / water / 4 h / 5 - 20 °C

2.2: 3 h / 0 - 10 °C

3.1: potassium carbonate; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); iso-butanol / water / 2 h / 65 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; iso-butanol; sodium nitrite; In water; 3.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.joc.8b02351

upstream raw materials:

1-(1-(imidazo[1,2-a]pyridin-6-yl)ethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine

1-(imidazo[1,2-a]pyridin-6-yl)ethanamine

methyl 6-aminonicotinoate

methyl 6-imidazo<1,2-a>pyridinecarboxylate

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF SAVOLITINIB AND ITS INTERMEDIATES". Page/Page column 38. . Retrieved 2021/11/20.
• 2、 Jia, Hong,Dai, Guangxiu,Weng, Jianyang,Zhang, Zhulin,Wang, Qing,Zhou, Feng,Jiao, Longxian,Cui, Yumin,Ren, Yongxin,Fan, Shiming,Zhou, Jinghong,Qing, Weiguo,Gu, Yi,Wang, Jian,Sai, Yang,Su, Weiguo. "Discovery of (S)-1-(1-(Imidazo[1,2- a ]pyridin-6-yl)ethyl)-6-(1-methyl-1 H -pyrazol-4-yl)-1 H -[1,2,3]triazolo[4,5- b ]pyrazine (Volitinib) as a Highly Potent and Selective Mesenchymal-Epithelial Transition Factor (c-Met) Inhibitor in Clinical Development for Treatment of Cancer". . p. 7577 - 7589. Retrieved 2014/12/11.