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Facile Synthesis of Dabigatran Etexilate Mesylate, an Anticoagulant Drug, Using a Novel Synthon, N-Hexyl-4-nitrophenyl Carbonate

Facile Synthesis of Dabigatran Etexilate Mesylate, an Anticoagulant Drug, Using a Novel Synthon, N-Hexyl-4-nitrophenyl Carbonate

Pavankumar V Solanki, Sekhar Babu Uppelli, Ravin B Patil, Pramod A Dhokrat, Saroj R Bembalkar, Vijayavitthal T Mathad

ACS Omega. 2018 May 29;3(5):5744-5753.

PMID: 31458774

Abstract:

Facile synthesis for Dabigatran etexilate mesylate (1), an anticoagulant drug, is reported using a novel synthon, n-hexyl-4-nitrophenyl carbonate (32), which substantially eliminates the formation of potential impurities 20-27, which were generated due to the use of n-hexyl chloroformate in previously reported methods. Pinner reaction to prepare a key and critical intermediate, amidine 8, was optimized using design of experiment software to establish critical process parameters to achieve 8 in 97% yield. Nucleophilic substitution of 8 with novel synthon n-hexyl-4-nitrophenyl carbonate (32) furnished the dabigatran base 9, which was then converted to its mesylate salt using methane sulfonic acid to provide 1 with an overall yield of 66% over three steps.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP6092542	Hexyl chloroformate		6092-54-2	Price

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