Emupertinib

CAS 2472802-77-8

MFC30H26N8O MW514.6 g/mol

2-Pyrazinecarboxamide, N-[4-[4-amino-6-ethynyl-5-(3-quinolinyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]bicyclo[2.2.1]hept-1-yl]-5-methyl-

N-{4-[4-amino-6-ethynyl-5-(quinolin-3-yl)-7Hpyrrolo[2,3-d]pyrimidin-7-yl]bicyclo[2.2.1]heptan-1-yl}-
5-methylpyrazine-2-carboxamide
epidermal growth factor receptor tyrosine kinase, inhibitor, antineoplastic, TAS3351, TAS 3351, CU9YW8A5TP

Emupertinib is a potent, small-molecule epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor. It possesses selective antineoplastic potential for targeting specific mutant profiles of cancer cells. The compound was originally developed by Taiho Pharmaceutical Co., Ltd. under the developmental code TAS3351

Development Profile

The International Nonproprietary Name (INN) for this therapeutic chemical structure was formally proposed under the World Health Organisation (WHO) proposed INN list 132 in early 2025. Global research pipelines list the compound’s structural classification profile within non-small cell lung cancer (NSCLC) primary discovery programs. The drug currently remains a specialized compound designated for global laboratory research use only, rather than standard human prescription or veterinary clinical treatments

SYN

[WO2020166680A1]

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020166680&_cid=P10-MP6AER-83942-1

[0184][Example 37]

N-(4-(4-amino-6-ethynyl-5-(quinoline-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-7-yl)bicyclo[2.2.1]heptan-1-yl)
　-5-methylpyrazine-2-carboxamide The title compound was obtained by following the same method as in Example 29 (step 6), except that 5-methylpyrazine-2-carboxylic acid was used instead of 5-(fluoromethyl)-2-methylpyrazole-3-carboxylic acid used in Example 29.

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2023204303&_cid=P10-MP6AER-83942-1

(Step 4)
Synthesis of N-(4-(4-amino-6-ethynyl-5-(quinoline-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-7-yl)bicyclo[2.2.1]heptan-1-yl)-5-methylpyrazine-2-carboxamide (compound (1))
[Chemical Formula 7]

It can be obtained by deprotecting the acetylene protecting group TES of N-(4-(4-amino-5-(quinoline-3-yl)-6-((triethylsilyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidine-7-yl)bicyclo[2.2.1]heptan-1-yl)-5-methylpyrazine-2-carboxamide obtained in Step 3 under basic conditions.
　The reagents used to create basic conditions are not particularly limited as long as the reaction proceeds, but examples of inorganic bases include metal hydroxides (sodium hydroxide, calcium hydroxide, etc.), metal hydrides (lithium hydride, sodium hydride, etc.), and metal carbonates (sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, lithium carbonate, magnesium carbonate, sodium bicarbonate, etc.). Examples of organic bases include metal alkoxides (sodium methoxide, potassium tert-butoxide, etc.), metal amides (sodium amide, lithium diisopropylamide, etc.), alkyl metal compounds (n-butyllithium, trimethylaluminum, etc.), alkylamines (triethylamine, tetramethylethylenediamine, piperidine, 1,4-diazabicyclo[2.2.2]octane, etc.), heterocyclic amines (diazabicycloundecene, pyridine, imidazole, etc.), and quaternary ammonium fluorides (tetra-n-butylammonium fluoride). Preferably, the reagent used to create basic conditions is a reagent that does not contain fluoride ions, more preferably a metal carbonate, and even more preferably potassium carbonate. These can be used alone or in combination to adjust the pH to the desired level.
　The amount of reagent used is not particularly limited as long as the reaction proceeds, but for example, 0.1 to 50 moles can be used per mole of the starting compound (the compound represented by formula (II)). Preferably, 0.1 to 10 moles, and more preferably 0.1 to 2 moles.

ADVT

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References

Substituted pyrrolo[2,3-d]pyrimidines as EGFR inhibitors

Publication Number: US-11786534-B2

Priority Date: 2019-02-15

Grant Date: 2023-10-17

• Crystal of 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: EP-4512808-A1Priority Date: 2022-04-22
• 7H-pyrrolo[2,3-d]pyrimidin-4-amine derivativePublication Number: KR-102645237-B1Priority Date: 2019-02-15Grant Date: 2024-03-07
• 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: WO-2020166680-A1Priority Date: 2019-02-15
• 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: US-2022160719-A1Priority Date: 2019-02-15
• 7H-Pyrrolo[2,3-d]pyrimidin-4-amine derivativesPublication Number: CN-113453764-BPriority Date: 2019-02-15Grant Date: 2024-04-16
• Brain-migrating tumor treatment agent containing, as active ingredient, n-(4-(4-amino-6-ethynyl-5-(quinolin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-7-yl) bicyclo[2.2.1]heptan-1-yl)-5-methylpyrazine-2-carboxamide or salt thereofPublication Number: WO-2025127108-A1Priority Date: 2023-12-13
• Crystals of 7h-pyrrolo[2,3-d]pyrimidin-4-amine derivativesPublication Number: WO-2025072720-A1Priority Date: 2023-09-29
• Crystal of 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: WO-2023204303-A1Priority Date: 2022-04-22
• Method for producing 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: WO-2023204304-A1Priority Date: 2022-04-22
• Method for producing 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: US-2025270214-A1Priority Date: 2022-04-22

///////emupertinib, anax labs, epidermal growth factor receptor tyrosine kinase, inhibitor, antineoplastic, TAS3351, TAS 3351, CU9YW8A5TP