Hydrazine → HCID 66991218, compound

Participants

Reaction Conditions

Reaction Steps

Dissolved (3S,6R)-1-[6-[4-cyano-3-fluoro-5-(methyloxy)phenyl]-2-(methylamino)-4-pyrimidinyl]-6-methyl-N-(phenylmethyl)-3-piperidinecarboxamide (96 mg, 0.196 mmol) with Ethanol (2 mL) in a 5 mL sealable vial then added hydrazine (0.185 mL, 5.89 mmol). The reaction was capped and heat overnight at 100° C. The reaction was concentrated then dissolved in 1 mL of DMSO and purified on HPLC (HPLC condition: open-access Gilson using Unipoint software with a Varian Polaris 5u C18(2) 100A, 50×30.00 mm 5 micron. 10-minute run (35 ml/min, 28% ACN/H2O, 0.1% TFA to 53% ACN/H2O, 0.1% TFA) with UV detection at 254 nm). Product fractions were pooled and the volume was reduced by reduce pressure until most of the MeCN was removed then the aqueous saturated NaHCO3 (10 mL) added. The mixture was then extracted with EtOAc (3×10 mL). The organic was pooled, washed with saturated. NaCl, dried over MgSO4, filtered, and concentrated. Then transferred in to 40 mL vial then water was added then freeze-dried to isolate 36 mg of off white solid. LC-MS (ES) m/z=501 [M+H]+. 1H NMR (400 MHz, DMSO-d6) d ppm 1.17 (d, J=7.07 Hz, 3H) 1.67 (d, J=3.54 Hz, 2H) 1.75 (dd, J=12.88, 3.03 Hz, 1H) 1.80-1.93 (m, 1H) 2.31-2.42 (m, 1H) 2.83 (d, J=4.55 Hz, 3H) 2.98 (br. s., 1H) 3.94 (s, 3H) 4.31 (dd, J=9.73, 5.94 Hz, 2H) 4.78 (br. s., 1H) 5.03 (br. s., 2H) 6.56 (br. s., 2H) 6.94 (br. s., 1H) 7.28 (d, J=7.07 Hz, 2H) 7.31-7.37 (m, 2H) 7.51 (br. s., 1H) 8.50 (t, J=5.94 Hz, 1H)

Provenance & Evidence