HCID 86707702, compound → HCID 68291545, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of crude cis-3-(3-carbamoylpyrrolo[1,2-b]pyridazin-4-ylamino)-2,2-dimethylcyclopentyl methanesulfonate (from Step 1), 1,8-diazabiclo[5,4,0]undec-7-ene (0.235 mL, 1.561 mmol) and N,N-dimethylformamide (2 mL) was stirred at 130° C. for 2 h, cooled to room temperature and quenched with saturated sodium bicarbonate (3 mL). Following addition of ethyl acetate (80 mL), the mixture was washed with water, brine, dried (MgSO4), filtered and concentrated. Silica gel chromatography, eluting with 20 to 100% ethyl acetate in hexanes, gave the title compound (40 mg, 47% yield for 2 steps). 1H NMR (400 MHz, methanol-d4) δ ppm 10.70 (1 H, d, J=8.58 Hz), 7.87-8.20 (1 H, m), 7.57 (1 H, dd, J=2.64, 1.54 Hz), 6.99 (1 H, dd, J=4.73, 1.43 Hz), 6.67 (1 H, dd, J=4.62, 2.86 Hz), 5.60-5.87 (2 H, m), 4.47-4.64 (1 H, m), 2.78-3.15 (1 H, m), 2.23-2.51 (1 H, m), 1.01-1.24 (6 H, m); MS (ES+) m/z:=271.2 (M+H).

Provenance & Evidence