Bavtavirine

Bavtavirine, CAS 1956373-71-9

• KAJ2CK6ZYE
• 4-((4-Amino-8-(4-((1E)-2-cyanoethenyl)-2,6-dimethylphenyl)-2-quinazolinyl)amino)benzonitrile
• Benzonitrile, 4-((4-amino-8-(4-((1E)-2-cyanoethenyl)-2,6-dimethylphenyl)-2-quinazolinyl)amino)-

C₂₆H₂₀N₆ 416.48

Benzonitrile, 4-[[4-amino-8-[4-[(1E)-2-cyanoethenyl]-2,6-dimethylphenyl]-2-quinazolinyl]amino]-

Gilead Sciences, Inc.; Institute of Organic Chemistry and Biochemistry of the AS CR, v.v.i.

Bavtavirine is a potent non-nucleoside reverse transcriptase inhibitors (NNRTIs). Bavtavirine is part of highly active antitiretroviral therapy (HAART) treatment regimen. Bavtavirine can be used for HIV disease research.

SCHEME

PATENT

WO2016105564

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2016105564&_cid=P11-M8QXHF-67832-1

A mixture of compound 2a (100 mg, 0.30 mmol), 4-cyanoaniline (46 mg, 0.388 mmol, Sigma-Aldrich) and hydrogen chloride solution in 1,4-dioxane (4M, 7 μL, 0.03 mmol) in dry N-methyl-2-pyrrolidone (2 mL) was heated at 120 °C for 2 hours. The reaction mixture was cooled down to room temperature and triethylamine (0.1 mL, 0.72 mmol) was added. After 15 minutes, water (5 mL) was added and the solid product was filtered off and washed with water. The crude residue was taken up in a mixture of dichloromethane and diethyl ether (1:1,5 mL) and then treated in a sonic bath for 3 minutes. The solid compound was filtered off and washed with diethyl ether (5 mL) to afford the title compound 2. ¹H NMR (400 MHz, DMSO-d₆) δ 9.44 (s, 1H), 8.18 (dd, J = 8.2, 1.5 Hz, 1H), 7.74 (d, J = 16.7 Hz, 1H), 7.70 (d, J = 8.9 Hz, 2H), 7.51 (s, 2H), 7.48 (dd, J = 7.1, 1.3 Hz, 1H), 7.34 (dd, J = 8.2, 7.1 Hz, 1H), 7.26 (d, J = 8.9 Hz, 2H), 6.54 (d, J = 16.7 Hz, 1H), 1.91 (s, 6H). HRMS: (ESI+) calculated for C₂₆H₂,N₆ [M+H] 417.1822, found 417.1820. LCMS (m/z) 417.2 [M+H], Tr = 4.68 min (LCMS method 1).

[1]. Jansa P, et al. Quinazoline derivatives used to treat hiv. The United States, WO2016105564 A1. 2016-06-30.

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