ChemicalBook CAS DataBase List beta-lactamase-IN-1

beta-lactamase-IN-1 synthesis

7synthesis methods

Product Name:beta-lactamase-IN-1
CAS Number:1075237-97-6
Molecular formula:C11H13N3O4
Molecular Weight:251.24

4-(2,2-Dimethyl-1,3-Dioxan-5-Yl)-6-Methoxypyrido[2,3-B]Pyrazin-3(4H)-One(WXC01734)

1075237-96-5
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1075237-97-6
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Yield: 91%

Reaction Conditions:

Stage #1:4-(2,2-dimethyl-1,3-dioxan-5-yl)-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one with hydrogenchloride;water in tetrahydrofuran at 20; for 1 h;
Stage #2: with sodium hydrogencarbonate in tetrahydrofuran;water; pH=~ 8

Steps:

2.g
(g) 4-[2-Hydroxy-1-(hydroxymethyl)ethyl]-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one4-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one (17.40 g, 59.7 mmol) was dissolved in THF (220 ml) to give a dark yellow solution. 1M HCl aq. (200 ml) was added (transient blue and green colours appeared in the solution) and the now light yellow solution was stirred at room temperature for 1 h. The mixture was concentrated to ca. 300 ml on a rotary evaporator using a cold water bath (some solid was precipitated during this procedure) then was stirred vigorously while solid sodium hydrogen carbonate was added in portions (caution: effervescence) until the mixture was ca. pH 8. The resulting yellow solid was collected by filtration with suction, washed with water (2×20 ml) and air-dried to give the title compound as an amorphous yellow solid (13.805 g, 91%).[ES MS] m/z 252 (MH⁺).

References:

Alemparte-Gallardo, Carlos;Barfoot, Christopher;Barros-Aguirre, David;Cacho-Izquierdo, Monica;Fiandor Roman, Jose Maria;Hennessy, Alan Joseph;Pearson, Neil David;Remuinan-Blanco, Modesto Jesus US2009/306089, 2009, A1 Location in patent:Page/Page column 16-17

1,3-Propanediol, 2-[(6-methoxy-3-nitro-2-pyridinyl)amino]-

757186-96-2
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1075237-97-6
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References

38533-61-8 Synthesis

38533-61-8
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1075237-97-6
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References

1075237-91-0 Synthesis

N-(2,2-Dimethyl-1,3-Dioxan-5-Yl)-6-Methoxy-3-Nitropyridin-2-Amine

1075237-91-0
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1075237-97-6
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References

N2-(2,2-Dimethyl-1,3-Dioxan-5-Yl)-6-Methoxypyridine-2,3-Diamine

1075237-92-1
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1075237-97-6
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References