Sodium Hydroxide → HCID 57654491, compound

Participants

Reaction Steps

The compound prepared in step e was dissolved in a 2:1 THF/methanol (3 mL) mixture and treated with 2N NaOH (0.15 mL). The mixture was stirred for 3 hours at RT, evaporated in vacuo, diluted with water (10 mL), and acidified with 6 N HCl to pH 2. The white solid precipitates were collected, dried under reduced pressure, dissolved in DMF (2 mL) and treated with HATU (0.0.62 g, 0.16 mmol), HOBt (0.013 g, 0.09 mmol) and DIEA (0.06 mL, 0.32 mmol) respectively. The resulting mixture was stirred at RT for 30 minutes and N-Methylpiperazine (0.014 mL, 0.14 mmol) was added. Stirring was continued for an additional hour and water (20 mL) was added. Dichloromethane (20 mL) was added and layers separated. The CH2Cl2 layer was dried over MgSO4, evaporated in vacuo and chromatographed (CH2Cl2/0-10% MeOH) to yield a solid product. Recrystallization for EtOAc afforded the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.60 (d, J=9.8, 1H), 8.17-8.07 (m, 4H), 7.79 (d, J=9.1 Hz, 1H), 7.65 (dd, J=8.5, 2.1 Hz, 1H), 7.50 (d, J=3.9 Hz, 1H), 7.08 (s, 1H), 3.67 (m, 4H), 3.34 (m, 4H), 2.32 (s, 3H); MS (m/z): 495 (MH+)

Provenance & Evidence