As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1057682-05-9, name is (R)-6-(3-Methylpiperazin-1-yl)nicotinonitrile, molecular formula is C11H14N4, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. HPLC of Formula: C11H14N4
To a stirred solution of 3-(6-fluoro-4-oxo-3H-quinazolin-2-yl)propanoic acid (5.0 g, 21.19mmol, obtained from Example 29, step 3) in dry DMF (40 mL, -8 vol), 6-[(3R)-3-methylpiperazine-1-yl]-pyridine-3-carbonitrile ( 4.06 g, 20 mmol), EDClHCl (6.08 g, 31.6 mmol),HOBt (3.43 g, 25.4 mmol) and DIPEA (14.5 mL, 84.5 mol) were added at 10-15C andstirred for 22 h. The reaction mixture was quenched with ice cold water (500 mL) andextracted with EtOAc (3 x 70 mL). The combined organic layers were dried over anhydrousNa2S04 and concentrated under reduced pressure to get crude compound. Crude compoundwas stirred with EtOAc (50 mL) for 1 hour at RT, filtered and suck dried. Solid obtained wasagain made slurry with EtOAc. Filtered the solid and washed with EtOAc (50 mL) to afford(50 mL) 6-[(3R)-4-[3-(6-fluoro-4-oxo-3H-quinazolin-2-yl)propanoyl]-3-methyl-piperazin-1-yl]pyridine-3-carbonitrile in 43% yield (3.8g). Chiral HPLC was used to confirm that thecompound is the enantiomer of compound 29. Column used: Lux,5 micron, Cellulose-4 (250X 4.6 mm , 5 micron , Mobile phase: 50:50 n-hexane:(0.1% HCOOH in 1:1ethanol:methanol), Flow rate: 1.0 mL/min, Temperature: 25C. Retention time for Renantiomer= 12.9 min; Retention time for compound 29 = 13.4 min.
With the rapid development of chemical substances, we look forward to future research findings about 1057682-05-9.
Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
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