ChemicalBook CAS DataBase List Etravirine

Etravirine synthesis

10synthesis methods

Product Name:Etravirine
CAS Number:269055-15-4
Molecular formula:C20H15BrN6O
Molecular Weight:435.28

Etravirine, also known as TMC 125 and R 165335, is a drug used for the treatment of HIV. Etravirine is a non-nucleoside reverse transcriptase inhibitor (NNRTI). It was also approved in 2008. Etravirine, in combination with other anti-retrovirals, is indicated for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in antiretroviral treatment-experienced adult patients, who have evidence of viral replication and HIV-1 strains resistant to a non-nucleoside reverse transcriptase inhibitor (NNRTI) and other antiretroviral agents.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

ROUTE 10

Process for the preparation of 4- [6-amino-5-bromo-2- [(4-cyanophenyl) amino]-4-pyrimidinyl]oxy]-3.5-dimethylbe nzonitrile (Etravirine); Rajan, Srinivasan Thirumalai; Eswaraiah, Sajja; Gutta, Madhusudhan; Peri, Seetha Rama Sarma; Assignee MSN Laboratories Private Limited, India; 2016; Patent Information; Apr 21, 2016; WO 2016059646 A2

269055-76-7 Synthesis

269055-76-7
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269055-15-4
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Yield:269055-15-4 40.5%

Reaction Conditions:

in water;

Steps:

A.19 EXAMPLE A19

EXAMPLE A19 4-[[5-bromo4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]benzonitrile (0.00250 mol) and NH₃/1,4-dioxane 0.5M (0.015 mol) were heated in a pressure vessel at 150° C. for 4 days. The sample was allowed to sit at ambient conditions for 2 days. Water was added slowly to the mixture until a precipitate formed. The mixture was stirred for 2 hours and filtered. The solid was recrystallized from CH₃CN to obtain 0.58 g (fraction 1). The filtrate was evaporated (fraction 2). Both fractions were combined and purified by column chromatography, eluding with CH₂Cl₂. The resulting residue of the desired fraction was recrystallized from CH₃CN to yield 0.44 g of 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile (40.5%).

References:

US2003/186990,2003,A1