Dimethylformamide → HCID 57791846, compound

Participants

Reaction Conditions

Reaction Steps

(Z)-6-chloro-3-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzylidene)isobenzofuran-1(3H)-one (67) (25 mg, 0.06 mmol) was taken up in water (1 mL) and N,N-dimethylformamide (0.5 mL) and treated with Hydrazine monohydrate (20 μL, 0.41 mmol). The resulting mixture was stirred at 105° C. for 1 hour. The reaction mixture was cooled and diluted with water (˜5 mL) and mixture extracted with DCM (2×5 mL). Combined organics were evaporated to dryness to afford the crude product, which was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and acetonitrile as eluents. Fractions containing the desired compound were evaporated to dryness to afford the desired material as a white foam (10 mg, 39% yield); 1H NMR (400.132 MHz, DMSO) δ 1.26-1.35 (1H, m), 1.40-1.49 (1H, m), 1.67-1.74 (1H, m), 1.83-1.90 (1H, m), 2.99-3.06 (1H, m), 3.26 (3H, s), 3.26-3.36 (2H, m), 3.39-3.45 (1H, m), 3.88-3.95 (1H, m), 4.33 (2H, s), 7.22 (1H, t), 7.31 (1H, dd), 7.38-7.42 (1H, m), 7.94 (1H, dd), 8.00 (1H, d), 8.21 (1H, d), 12.72 (1H, s); m/z (LC-MS, ESI+), RT=2.23 (M+H 430.7).

Provenance & Evidence