Sodium Hydroxide → HCID 59599436, compound

Participants

Reaction Conditions

Reaction Steps

To a reaction solution of compound (4-6) (377 mg, 0.76 mmol) in 5.0 mL of MeOH at room temperature under N2 was added another solution of 2.0 N NaOH (2) (1.5 mL, 3.04 mmol). The resulting mixture was stirred at 80° C. for 3 hours. The reaction mixture was concentrated by vacuum to remove most of the MeOH and acidified by 2 M HCl to pH 4.0. The mixture was extracted with CH2Cl2 (2×200 mL); the organic layers were washed with brine (50 mL), and dried (Na2SO4) and concentrated by vacuum to give 324 mg of (4-7) as a yellow solid. (92% yield). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.92-1.04 (m, 2H) 1.57-1.72 (m, 2H) 1.76-1.90 (m, 3H) 3.98-4.18 (m, 2H) 6.46 (s, 2H) 6.89-7.02 (m, 1H) 7.29-7.52 (m, 2H) 7.52-7.63 (m, 2H) 7.73 (d, J=1.52 Hz, 1H) 7.94 (s, 1H) 12.19 (s, 1H). LCMS calcd for C21H19Cl2FN4O3(M−H) 463, found 463. HPLC purity 87%.

Provenance & Evidence