Sodium Carbonate → HCID 24889465, compound

Participants

Reaction Conditions

Reaction Steps

This compound may be prepared using methods as described for Compound 6, step 4, using 5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(morpholin-4-yl)-phenyl]-amine (100 mg, 0.267 mmol), 1H-pyrazole-2-boronic acid (60 mg, 0.535 mmol), Pd(PPh3)4 (93 mg, 0.08 mmol) and Na2CO3 (88 mg, 0.80 mmol) in DMF (2 mL). The reaction mixture is placed in a stem-tube and stirred at 100° C. for 18 hours. After cooling, the mixture is diluted with NaHCO3 solution and extracted with EtOAc (4×). The organic layer is washed with water, dried over MgSO4, filtered and evaporated to afford a crude product that is purified by silica gel column chromatography eluting with DCM followed by 96:4 DCM:NH3 (7M in MeOH). The title compound is isolated after trituration with diethyl ether (12.4 mg, 13%). Conversion into the mesylate salt using 0.1M methanesulfonic acid (0.342 mL, 0.0342 mmol) gives the target compound (10 mg, 81%). 1H-NMR (400 MHz, d6-DMSO) δ(ppm) 2.34 (3H, s, MsOH), 3.14 (4H, m), 3.81 (4H, m), 7.04 (2H, d), 7.27 (1H, m), 7.92 (3H, m), 8.24 (1H, s), 8.76 (1H, s), 9.92 (1H, s). LCMS: Rt 2.45 min (97.6%), m/z (APCI) 363 (M+H)+.

Provenance & Evidence