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Sotorasib

Catalog Number: EVT-259089

CAS Number: 2296729-00-3

Molecular Formula: C30H30F2N6O3

Molecular Weight: 560.6058

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Sotorasib, also known as AMG-510, is an experimental KRAS inhibitor being investigated for the treatment of KRAS G12C mutant non-small cell lung cancer, colorectal cancer, and appendix cancer. It is used in adults to treat non-small cell lung cancer who have already been treated with at least one other cancer medicine. Sotorasib is given when the cancer has progressed or has spread to other parts of the body or when surgery is not an option.

Synthesis Analysis

In the development of Sotorasib, an axially chiral biaryl moiety proved a critical structural element in engaging a “cryptic” protein binding pocket and enhancing inhibitor potency. The decision to develop sotorasib as a single-atropisomer drug gave rise to a range of analytical and synthetic challenges. The synthetic challenge centered on the large-scale synthesis of an atropisomerically pure building block comprising the central azaquinazolinone and pyridine rings of sotorasib.

Chemical Reactions Analysis

Sotorasib demonstrated a 10-fold difference in potency due to restricted rotation about the axis of chirality, giving rise to configurationally stable atropisomers. The resolution process was subsequently refined to enable thermal recycling of the undesired atropisomer.

Physical And Chemical Properties Analysis

Sotorasib has a molecular formula of C30H30F2N6O3 and a molecular weight of 560.606. It should be stored at room temperature in a dry place.

Properties

CAS Number

2296729-00-3

Product Name

Sotorasib

IUPAC Name

6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-propan-2-ylpyridin-3-yl)-4-[(2S)-2-methyl-4-prop-2-enoylpiperazin-1-yl]pyrido[2,3-d]pyrimidin-2-one

Molecular Formula

C30H30F2N6O3

Molecular Weight

560.6058

InChI

InChI=1S/C30H30F2N6O3/c1-6-23(40)36-12-13-37(18(5)15-36)28-19-14-21(32)26(24-20(31)8-7-9-22(24)39)34-29(19)38(30(41)35-28)27-17(4)10-11-33-25(27)16(2)3/h6-11,14,16,18,39H,1,12-13,15H2,2-5H3/t18-/m0/s1

InChI Key

NXQKSXLFSAEQCZ-SFHVURJKSA-N

SMILES

CC1CN(CCN1C2=NC(=O)N(C3=NC(=C(C=C32)F)C4=C(C=CC=C4F)O)C5=C(C=CN=C5C(C)C)C)C(=O)C=C

Solubility

Soluble in DMSO

Synonyms

AMG-510 racemate; AMG 510; AMG-510; AMG510;

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