2-Pyrazinecarbonitrile, 5-[[5-(2-hydroxy-6-methoxyphenyl)-1H-pyrazol-3-yl]amino]- synthesis

4synthesis methods

Product Name:2-Pyrazinecarbonitrile, 5-[[5-(2-hydroxy-6-methoxyphenyl)-1H-pyrazol-3-yl]amino]-
CAS Number:1234015-69-0
Molecular formula:C15H12N6O2
Molecular Weight:308.29

2-Pyrazinecarbonitrile, 5-[[5-[2-methoxy-6-[(4-methoxyphenyl)methoxy]phenyl]-1H-pyrazol-3-yl]amino]-

1234015-68-9
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2-Pyrazinecarbonitrile, 5-[[5-(2-hydroxy-6-methoxyphenyl)-1H-pyrazol-3-yl]amino]-

1234015-69-0
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Yield:1234015-69-0 87 %

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane at 65;

Steps:

Step 5: 5-((5-(2-Hydroxy-6-methoxyphenyl)-1H-pyrazol-3-yl)amino)pyrazine-2-carbonitrile (P1-1)

A solution of 5-((5-(2-methoxy-6-((4-methoxybenzyl)oxy)phenyl)-1H-pyrazol-3-yl)amino)pyrazine-2-carbonitrile (8 g, 18.7 mmol) and hydrogen chloride (4M in 1,4-dioxane, 80 mL, 320 mmol) was heated to 65 °C for 5 hours. The brown slurry was cooled to room temperature. The precipitate was collected and the solid was washed with ethyl acetate (150 mL) to afford the title compound as the dihydrochloride salt (7 g, 18.4 mmol). The product (7 g) was suspended in tetrahydrofuran (100 mL). To the mixture was added triethylamine (4.65 g, 46 mmol) and the resulting slurry was stirred at room temperature for 2 hours. The mixture was filtered and the filtrate was evaporated. The residue was suspended in diethyl ether (20 mL) and the mixture was stirred at room temperature for 30 minutes. The precipitate was collected to afford the title compound (5 g, 87% yield) as a yellow solid. LCMS: Rt = 1.160 min, ESMS m/z = 308.8 [M+H]⁺.1H NMR (400 MHz, DMSO-d6) δ ppm 10.83 (s, 1H), 8.65 (s, 1H), 8.56 (s, 1H), 7.15 (t, J = 8.4 Hz, 1H), 6.86 (s, 1H), 6.61 (d, J = 8.4 Hz, 1H), 6.58 (d, J = 8.4 Hz, 1H), 3.79 (s, 3H).

References:

WO2022/251502,2022,A1 Location in patent:Paragraph 00154

113305-94-5
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1234015-69-0
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References

1234015-62-3 Synthesis

2-Propen-1-one, 1-[2-methoxy-6-[(4-methoxyphenyl)methoxy]phenyl]-3,3-bis(methylthio)-

1234015-62-3
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1234015-69-0
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References

2-Pyrazinecarbonitrile, 5-[[(1E)-3-[2-methoxy-6-[(4-methoxyphenyl)methoxy]phenyl]-1-(methylthio)-3-oxo-1-propen-1-yl]amino]-

1234015-67-8
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1234015-69-0
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References