Potassium Hydroxide → HCID 57731584, compound

Participants

Reaction Steps

1-iso-Propyl-piperidine-3-carboxylic acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-amide (185.1 mg, 0.27 mmol) was dissolved in methanol (0.5 mL) and dimethylformamide (0.5 mL), cooled to 0° C. and 50% w/v aqueous potassium hydroxide (0.2 mL) was added. After 1 hour, the reaction was quenched by addition of concentrated hydrochloric acid (0.2 mL). The mixture was carefully poured into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and dried to a residue which was purified by preparative HPLC to afford 1-isopropyl-piperidine-3-carboxylic acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-amide (46.0 mg, 31.9%). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 0.98 (d, J=6.5 Hz, 6H), 1.59 (m, 2H), 1.76 (m, 2H), 2.16 m, 3H, 2.32 (m, 2H), 2.70 (m, 1H, 2.87 (s, 3H), 2.97 (s, 3H, 3.82 (s, 3H), 7.04 (t, J=7.5 Hz, 1H), 7.09 (d, J=8.0 Hz, 1H), 7.28 (dt, J=1.5, J=7.5 Hz 1H), 7.61 (dd, J=1.5 Hz, J=7.5 Hz, 1H), 7.59-7.61 (m, 2H), 7.65 (d, J=8.0 Hz, 1H), 7.72-7.74 (m, 2H), 8.54 (d, J=2.5 Hz, 1H), 9.51 (s, 1H), 11.92 (s, 1H). MS: m/z 541 (M+H+).

Provenance & Evidence