Ammonia → HCID 49784990, compound

Participants

Reaction Conditions

Reaction Steps

2 M NH3 in 2-propanol (2.00 mL, 92 mmol) was added to N-(3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-amine (97 mg, 0.159 mmol) and the mixture was sealed and heated at 90° C. overnight. After cooling, the precipitate was collected and dried to give a yellow solid which was dissolved in DCM (3.00 mL, 46.6 mmol) and then TFA (1.50 mL, 19.47 mmol) was slowly added. The mixture was stirred at rt for 1 h and then concentrated, adsorbed onto a plug of silica gel and chromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr., pre-packed silica gel column (DCM to 10% MeOH in DCM) to give N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)-1H-indazol-4-amine (18 mg, 0.036 mmol, 22.88% yield) as a yellow solid. LCMS (API-ES) m/z 495 (M+H)+; 1H NMR (400 MHz, d6-DMSO) δ 13.10 (br. s., 1H) 12.27 (s, 1H) 8.75 (s, 1H) 8.32 (br. s., 1H) 8.19 (s, 1H) 8.13 (d, J=7.04 Hz, 1H) 7.78 (br. s., 2H) 7.31 (t, J=8.31 Hz, 1H) 7.15 (d, J=8.22 Hz, 1H) 3.53 (s, 2H) 3.12 (br. s., 4H) 2.87 (s, 3H) 2.57 (s, 3H) 2.37-2.49 (m, 4H).

Provenance & Evidence