Trifluoroacetic acid → HCID 71625974, compound

Participants

Reaction Steps

To a solution of tert-butyl (3R,4R)-4-(5-(6-tert-butylpyridin-2-ylamino)-6-carbamoylpyridazin-3-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (73 mg, 150 μmol) in CH2Cl2 (3.00 mL) was added TFA (1.48 g, 1 mL, 13.0 mmol) and the mixture stirred to room temperature for 18 h. The solvent was evaporated and the residue purified by flash chromatography (spherical silica 20-45 μM, 23 g, Versaflash Supelco) eluting with 0 to 5% over 20 min (MeOH containing 10% NH4OH)/CH2Cl2 to give 6-((3R,4R)-3-aminotetrahydro-2H-pyran-4-ylamino)-4-(6-tert-butylpyridin-2-ylamino)pyridazine-3-carboxamide (23.5 mg, 40.5% yield) as an off-white solid. 1H NMR (CHLOROFORM-d) δ: 11.45 (s, 1H), 8.38 (s, 1H), 8.03 (br. s., 1H), 7.54 (t, J=7.9 Hz, 1H), 6.93 (d, J=7.6 Hz, 1H), 6.69 (d, J=7.9 Hz, 1H), 5.83 (d, J=8.3 Hz, 1H), 5.37 (br. s., 1H), 3.91-4.13 (m, 2H), 3.86 (d, J=11.0 Hz, 1H), 3.65 (d, J=10.6 Hz, 1H), 3.41-3.58 (m, 1H), 3.04 (br. s., 1H), 1.97 (d, J=9.4 Hz, 1H), 1.63-1.85 (m, 1H), 1.55 (br. s., 3H), 1.42 (s, 9H); LC-MS 386.2 [M+H]+.

Provenance & Evidence