Sodium Thiosulfate → HCID 56848810, compound

Participants

Reaction Steps

To 2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline-7-carboxamide (203 mg, 0.55 mmol) in DCM (5 mL) at 0° C. was added 3-chloroperbenzoic acid (70%, 205 mg, 0.84 mmol) and the mixture was stirred for 90 min. An additional amount of 3-chloroperbenzoic acid (70%, 68 mg, 0.28 mmol) was then added and the mixture was stirred for 15 min. The mixture was diluted with DCM and then aq sodium thiosulfate was added, followed by saturated aq sodium bicarbonate. The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure. To the residue were added THF (5 mL) and 5-methyl-1H-pyrazol-3-amine (160 mg, 1.65 mmol) and the mixture was stirred at rt for 20 min and then concentrated under reduced pressure. The residue was purified by preparative HPLC (Varian diphenyl reverse phase column, eluted with gradient of solvent B=0.05% AcOH/ACN and solvent A=5% ACN/0.05% AcOH/H2O) to afford 2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-((5-methyl-1H-pyrazol-3-yl)amino)quinazoline-7-carboxamide (21 mg, 10%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.19 (s, 3H) 6.04 (s, 1H) 7.69 (s, 1H) 7.97-8.10 (m, 3H) 8.26-8.42 (m, 2H) 8.67 (s, 1H) 8.76 (d, J=8.67 Hz, 1H) 10.85 (br s, 1H) 12.20 (br s, 1H); LC-MS (ESI) m/z 414 (M+H)+.

Provenance & Evidence