Hydrochloric Acid → HCID 90446486, compound

Participants

Reaction Conditions

Reaction Steps

6-(2-(Diphenylmethylene)hydrazinyl)-2-methyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridine (9.3 g, 20.19 mmol) was dissolved in toluene (497 mL). Concentrated HCl (134 mL, 1608 mmol) was added and the reaction mixture was stirred for 1.5 h at 110° C., allowed to cool to RT, and stirred for 10 h. The organic phase was removed and the aqueous phase was extracted with toluene (1×100 mL). The combined organics were back extracted with 1 N HCl (1×100 mL). The combined aqueous phases were adjusted to pH ˜11 with 50% NaOH (aq), saturated with solid NaCl, and extracted with EtOAc (3×200 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo to afford 6-hydrazinyl-2-methyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridine (4.7 g, 79%) as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ 8.31 (d, J=5.7 Hz, 1H), 8.22 (s, 1H), 7.92 (s, 1H), 7.44 (s, 1H), 7.28 (d, J=8.8 Hz, 1H), 7.11 (d, J=2.4 Hz, 1H), 6.64 (d, J=8.8 Hz, 1H), 6.49 (dd, J=5.7, 2.4 Hz, 1H), 4.14 (s, 2H), 3.84 (s, 3H), 2.11 (s, 3H); MS (ESI) m/z: 297.1 (M+H+).

Provenance & Evidence