Potassium Hydroxide → HCID 58305287, compound

Participants

Reaction Steps

To a mixture of racemic (1S,2R) and (1S,2R)-2-(4-chlorophenyl)-1′-(1 H-imidazol-4-yl)spiro[cyclopropane-1,3′-indolin]-2′-one (0.4 mmol, 134 mg), methyl-bromoacetate (61.2 mg, 0.4 mmol) and 5 mg of TEBA (0.008 mmol) in 2 mL of DCM was added 50% KOH (0.5 mL). The reaction mixture was stirred at room temperature for 14 hours. Then the mixture was concentrated under reduced pressure and acidified to pH˜4. The residue was dissolved in 2 mL of DMF. Purification by preparative HPLC gave the title compound as a white powder (113 mg, 68%). LC/MS m/e calcd. for C21H16ClN3O3: 393, observed (M+H)+: 394.2 1H NMR (400 MHz, DMSO-d6) δppm 2.05-2.16 (m, 1 H) 2.39 (dd, J=7.96, 4.93 Hz, 1 H) 3.20 (t, J=8.72 Hz, 1 H) 4.97 (s, 2 H) 6.18 (d, J=7.07 Hz, 1 H) 6.79 (t, J=7.20 Hz, 1 H) 7.06-7.22 (m, 1 H) 7.38 (s, 4 H) 7.54 (d, J=1.01 Hz, 1 H) 7.69 (d, J=7.83 Hz, 1 H) 7.74 (d, J=1.26 Hz, 1 H). MS calcd. for C21H16ClN3O3 393, obsd. (ESI+) [(M+H)+] 394.3.

Provenance & Evidence