With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.35857-89-7,6-Chloropyridazine-3-carbonitrile,as a common compound, the synthetic route is as follows.
Raw (R)-2-bromo-7-((3,3-dimethylpiperidin-4-yl)amino)pyrazolo[1,5-a]pyrimidine- 6-carboxamide XI (2.05 g, 5.58 mmol) from Step 6 was dissolved in dry dimethylformamide (50 mL) under argon atmosphere. To the solution triethylamine (3.91 mL, 27.9 mmol) and then 6-chloropyridazine-3-carbonitrile (963 mg, 6.69 mmol) were added. Reaction mixture was heated at 80 C with stirring for 1 hour. After cooling to room temperature, 100 mL of water was added and the mixture was extracted with AcOEt (3 x 100 mL). Organic phases were combined, dried and evaporated under reduced pressure. To the residue toluene (50 mL) was added and evaporated under reduced pressure. This was repeated twice. The residue was purified by column chromatography (silica gel, eluent: dichloromethane: methanol = 98:2, v/v). Product was obtained as a light-yellow solid (2.35 g, 4.99 mmol) with the yield of 89%. MS-ESI: (m/z) calculated for C19H21BrN9O [M+H]+= 470.1, found 470.1. 1H NMR (300 MHz, CDCl3 ) delta 11.06 (d, J=8.3 Hz, 1H), 8.44 (s, 1H), 7.50 (d, J=9.7 Hz, 1H), 6.99 (d, J=9.7 Hz, 1H), 6.45 (s, 1H), 6.04 (bs, 2H), 5,49 (dd, J=10.6, 4.2 Hz, 1H), 4.48 (d, 3=133 Hz, 1H), 4,29 (d, J=13.6 Hz, 1H), 3.40 (ddd, J=13.6, 9.4, 3.3 Hz, 1H), 3.17 (d, 3=13 Hz, 1H), 2.26 (dq, 3=113, 3.6 Hz, 1H), 1.96-1.80 (m, 1H), 1.11 (s, 3H), 1.10 (s, 3H).
35857-89-7, The synthetic route of 35857-89-7 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; CELON PHARMA S.A.; MROCZKIEWICZ, Michal; STYPIK, Bartosz; BUJAK, Anna; SZYMCZAK, Krzysztof; GUNERKA, Pawel; DUBIEL, Krzysztof; WIECZOREK, Maciej; PIECZYKOLAN, Jerzy; (49 pag.)WO2018/206739; (2018); A1;,
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