Potassium Hydroxide → HCID 131734518, compound

Participants

Reaction Steps

To a suspension of ((5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridin-3-yl)sulfonyl)phosphoramidic acid (2) (0.030 g, 0.054 mmol) in ethanol (3 mL) was added KOH (9.0 mg, 0.16 mmol) in 0.5 mL of water. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 2 h. The reaction mixture was concentrated to dryness and the residue was washed with ethyl acetate (2×8 mL), acetone (2×8 mL) and acetonitrile (2×8 mL) to afford tri-potassium(5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridin-3-yl)sulfonylphosphoramidate (6) (0.028 g, 0.043 mmol, 78% yield) as a brown solid. 1H NMR (400 MHz, deuterium oxide) δ ppm 4.52 (s, 2H), 7.09 (d, J=7.78 Hz, 1H), 7.19-7.24 (m, 2H), 7.28-7.40 (m, 5H), 7.61-7.77 (m, 3H), 8.28 (d, J=4.27 Hz, 1H), 8.91 (t, J=1.88 Hz, 1H), 9.08 (d, J=2.26 Hz, 1H), 9.21 (d, J=1.76 Hz, 1H); LCMS Method A: retention time 1.60 min, [M+1]=549.2. HPLC Method B: Purity 96.0%, retention time 6.09 min, HPLC Method C: Purity 96.0%, retention time 5.86 min. Elemental analysis: MF C25H18N6SPO5.2.6 K.4.5 H2O, Calculated C 41.22; H, 3.72; N, 11.54; K, 14.12; H2O, 11.00; Found C, 40.79; H, 3.56; N, 11.17; K, 13.76; H2O, 10.49.

Provenance & Evidence