Water → HCID 59843064, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(4-(azidomethyl)-3-chlorophenyl)-2-(2-(7-methoxyquinolin-4-yloxy)ethyl)pyridazin-3(2H)-one (400 mg, 864 μmol) in THF (8 mL), MeOH (1 mL), and water (1 mL) was added sodium sulfide, nonahydrate (540 mg, 6913 μmol) and stirred overnight at 40° C. The reaction was then partitioned between DCM and 5% NaHCO3. The organic layer was dried over MgSO4, concentrated, then purified on silica (40 g) eluting with 0>6% of NH3 in MeOH (2 M)/DCM. The product was further purified on RP-HPLC eluting with ACN/water (0.1% TFA). Desired fractions concentrated under reduced pressure then residue partitioned between DCM and NaOH (1 M). The organic was then dried over MgSO4 and concentrated under reduced pressure to provide a white solid. MS (ESI pos. ion) m/z: 437 (MH+); calc'd for C23H21ClN4O3: 436. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.91 (s, 3 H) 3.99 (s, 2 H) 4.65 (t, J=5.38 Hz, 2 H) 4.80 (t, J=5.28 Hz, 2 H) 6.67 (d, J=5.48 Hz, 1 H) 6.98-7.09 (m, 2 H) 7.32 (d, J=2.35 Hz, 1 H) 7.48 (d, J=8.02 Hz, 1 H) 7.58 (dd, J=8.02, 1.76 Hz, 1 H) 7.64 (d, J=9.78 Hz, 1 H) 7.79 (d, J=1.76 Hz, 1 H) 8.02 (d, J=9.19 Hz, 1 H) 8.64 (d, J=5.28 Hz, 1 H)

Provenance & Evidence