Electric Literature of 82205-58-1 , The common heterocyclic compound, 82205-58-1, name is 1-(5-Nitropyridin-2-yl)piperazine, molecular formula is C9H12N4O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Example 86Synthesis of 4-[5-(acetylamino)pyridin-2-yl]piperazin-l-yl-5-(4~ fluorophenyl)-6-[4-(methylsulfonyl)phenyl]-2-(trifluoromethyl)pyrimidine4-Chloro-5-(4-fluorophenyl)-6-[4-(methylsulfonyl)phenyl]-2-(trifluoro methyl)pyrimidine (0.15g, 0.35mmol) was treated with l-(5-nitropyridin-2- yl)?iperazine (0.087g, 0.418mmol) and diisopropylethylamine (0.06mL, 0.35mmol), acetonitrile (2.5mL) and heated at 60-650C for 2 hours. Subsequently the reaction mixture was precipitated by the addition of diisopropyl ether (2mL). The above-obtained solid (0.1 Ig, 0.182mmol) was taken up in acetic acid (2mL) and tin (II) chloride dihydrate (0.123g, 0.182mmol) was added to it. Stirring was continued further for 11 hours, and then the reaction mixture was poured onto ice-cold water, and extracted with ethyl acetate (25mL x 2). After neutralization with sodium bicarbonate, the organic layer was evaporated to obtain the crude material, which was purified by column chromatography (2% MeOH in dichloromethane) to yield the title compound. 1H-NMR (DMSOd6) ?: 1.99 (s, 3H), 3.19 (s, 3H), 3.29 – 3.40 (m, 8H), 6.77 (d, IH), 7.19 – 7.23 (m, 2H), 7.31 – 7.34 (m, 2H), 7.36 (d, 2H), 7.74 (d, IH)5 7.80 (d, 2H), 8.24 (d, IH), 9.77 (s, IH, D2O exchangeable). MS m/z: 615.1 (M++l).
The synthetic route of 82205-58-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ORCHID RESEARCH LABORATORIES LIMITED; WO2007/83182; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem