Sodium Bicarbonate → HCID 59233146, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-3-(1-(6-chloropyridazin-3-yl)ethyl)-[1,2,4]triazolo[4,3-a]pyridine (650 mg, 1.920 mmol), (2,4-dimethoxyphenyl)methanamine (0.577 mL, 3.84 mmol), and NaHCO3 (645 mg, 7.68 mmol) in IPA (10.0 mL) was heated in a microwave on high absorbance for 18 hrs at 140° C. The reaction was cooled to ambient temperature, stripped to dryness via rotary evaporation, and reconstituted in EtOAc (25 mL). The insolubles were filtered off and the filtrate was reduced to dryness. The resulting residue was purified via MPLC (DCM:MeOH, 98:2) to provide the title compound, 6-(1-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)-N-(2,4-dimethoxybenzyl)pyridazin-3-amine 48E (750 mg, 1.598 mmol, 83% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.77 (d, J=7.07 Hz, 3 H) 3.72 (s, 3 H) 4.37 (d, J=5.81 Hz, 2 H) 4.95 (d, J=7.07 Hz, 1H) 6.44 (dd, J=8.34, 2.53 Hz, 1 H) 6.54 (d, J=2.27 Hz, 1 H) 6.85 (d, J=9.35 Hz, 1H) 7.03 (s, 1 H) 7.12 (d, J=8.34 Hz, 1 H) 7.29 (d, J=9.35 Hz, 1 H) 7.45 (dd, J=9.73, 1.64 Hz, 1 H) 7.69-7.79 (m, 1 H) 8.59 (s, 1 H). ESI-MS:m/z 469.2 (M+H)+.

Provenance & Evidence