Trifluoroacetic acid → HCID 71626971, compound

Participants

Reaction Steps

A solution of tert-butyl (1S,2R)-2-(6-carbamoyl-5-(6,7-dihydro-5H-cyclopenta[b]pyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (444 mg, 950 μmol) in CH2Cl2 (5 mL) was treated with TFA (4.08 g, 2.76 mL, 35.8 mmol) and the mixture stirred at room temperature for 18 h. The solvents were evaporated and the residue purified by flash chromatography (spherical silica 20-45 μM, 80 g, Versaflash Supelco) eluting with 0 to 5% of a 9:1 MeOH:NH4OH solution in CH2Cl2, 15 min) to give 6-((1R,2S)-2-aminocyclohexylamino)-4-(6,7-dihydro-5H-cyclopenta[b]pyridin-2-ylamino)pyridazine-3-carboxamide (80 mg, 23%) as an off-white solid. 1H NMR (DMSO-d6) δ: 11.54 (br. s., 1H), 8.35 (br. s., 1H), 7.95 (br. s., 1H), 7.46-7.69 (m, 2H), 6.80 (d, J=7.2 Hz, 1H), 6.69 (d, J=7.6 Hz, 1H), 3.89 (br. s., 1H), 3.12 (br. s., 1H), 2.75-2.98 (m, 4H), 1.96-2.17 (m, 2H), 1.61 (d, J=11.7 Hz, 8H), 1.31 (br. s., 2H); LC-MS 368.3 [M+H]+.

Provenance & Evidence