(1R,2R)-2-hydrazinylcyclohexan-1-ol

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl 1-[(6-methyl-2,3′-bipyridin-5-yl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate [(Example 6, Step 2), 47 mg, 0.11 mmol], (±)-trans-2-hydrazinocyclohexanol (44 mg, 0.34 mmol, 3 equiv), potassium carbonate (0.16 g, 1.1 mmol, 10 equiv) and mercury(II) chloride (31 mg, 0.11 mmol, 1 equiv) were combined in ethanol (10 mL) at ambient temperature and after 5 minutes, the mixture was warmed to 70° C. for 3 h. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (100 mL, aqueous saturated) and extracted with ethyl acetate (3×75 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative TLC (eluting with ethyl acetate containing 10% methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 9.02 (1H, d, J=2.1 Hz), 8.93 (1H, d, J=2.0 Hz), 8.75 (1H, dd, J=4.6, 1.8 Hz), 8.52 (1H, dd, J=8.1, 1.8 Hz), 8.16 (1H, dd, J=8.2, 2.4 Hz), 7.97 (1H, dd, J=8.3, 2.3 Hz), 7.66 (1H, dd, J=8.2, 0.6 Hz), 7.50 (1H, dd, J=8.0, 4.6 Hz), 7.23 (1H, d, J=8.0 Hz), 6.0 (1H, d, J=14.3 Hz), 5.96 (1H, d, J=14.3 Hz), 4.30 (1H, ddd, J=11.7, 9.8, 4.1 Hz), 4.07-4.01 (1H, m,), 2.60 (3H, s), 2.20 (1H, br d, J=10.3 Hz), 2.01 (1H, br d, J=11.9 Hz), 1.89-1.79 (2H, m), 1.72-1.53 (2H, m), 1.50-1.39 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 468.2142 [(M+H)+; calculated for C26H26N7O2: 468.2143]. The mixture was cooled to ambient temperature extracted with ethyl acetate (3×75 mL) The combined organic extracts were dried with sodium sulfate filtered concentrated in vacuo The residue was purified by preparative TLC (eluting with ethyl acetate containing 10% methanol)