Trifluoroacetic acid → HCID 71626104, compound

Participants

Reaction Steps

To a solution of tert-butyl (3R,4R)-4-(6-carbamoyl-5-(6-isopropoxypyridin-2-ylamino)pyridazin-3-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (185 mg, 379 μmol) in dichloromethane (5.9 mL) was added trifluoroacetic acid (865 mg, 585 μL, 7.59 mmol) and the mixture stirred at r.t. for 16 h. The mixture was diluted with 25% aqueous NH4OH, dichloromethane, and water. The organic phase was separated and washed with water (2×), then concentrated in vacuo and purified by chromatography (silica, 3 to 10% of a 99.5:0.5 methanol:NH4OH solution in dichloromethane) to give 6-((3R,4R)-3-aminotetrahydro-2H-pyran-4-ylamino)-4-(6-isopropoxypyridin-2-ylamino)pyridazine-3-carboxamide (68 mg, 176 μmol, 46%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (s, 1H), 8.38 (s, 1H), 7.62 (m, 3H), 6.76 (d, J=7.7 Hz, 1H), 6.54 (d, J=7.8 Hz, 1H), 6.35 (d, J=8.2 Hz, 1H), 5.18 (m, 1H), 4.07 (br. s, 1H), 3.80 (d, J=11.3 Hz, 1H), 3.67 (dd, J=11.6, 3.8 Hz, 1H), 3.50 (dd, J=11.9. 2.3 Hz, 1H), 3.39 (m, 2H), 2.96 (s, 1H), 1.78 (m, 1H), 1.68 (m, 2H), 1.33 (dd, J=6.3, 1.7 Hz, 6H); MS (EI/CI) m/z: 388.3 [M+H].

Provenance & Evidence