Sodium Hydroxide → HCID 66917791, compound

Participants

Reaction Steps

[1-Methyl-4-(naphthalen-2-yloxy)-1H-indazol-3-ylamino]-acetic acid (A25) To a 50 mL round-bottomed, one-necked flask containing K-3 (90 mg, 0.25 mmol) was added 1:1 EtOH/H2O (2 mL). To this stirring suspension was added 15% aqueous NaOH (0.133 mL, 0.5 mmol) and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was concentrated on the vacuum line and the resulting solid was suspended in H2O (2 mL) and 1N HCl was added until a pH of 1-2 (litmus paper) was reached. The mixture was stirred at room temperature for 30 min and then filtered. The resulting solid was dried to afford 65 mg (75%) of A25 as an off-white solid. 1H NMR (400 MHz, DMSO-d6) 3.77 (s, 3H), 3.93 (s, 2H), 5.63 (br s, 1H), 6.18 (d, J=7.6 Hz, 1H), 7.07 (d, J=8.0 Hz, 1H), 7.18 (dd, J=8.0, 8.0 Hz, 1H), 7.41 (dd, J=8.8, 1.2 Hz, 1H), 7.51 (m, 2H), 7.63 (d, J=2.4 Hz, 1H), 7.89 (d, J=8.0 Hz, 1H), 7.96 (d, J=7.6 Hz, 1H), 8.02 (d, J=8.8 Hz, 1H), 12.45 (br s, 1H), LC/MS (86%) (ESI+) Calcd. for 347.4; Found: 348.7 (M+1).

Provenance & Evidence