Trifluoroacetic acid → HCID 71626893, compound

Participants

Reaction Conditions

Reaction Steps

{(1S,2R)-2-[6-Carbamoyl-5-(1-methyl-1H-pyrrolo[2,3-b]pyridin-6-ylamino)-pyridazin-3-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (23 mg, 0.048 mmol) was dissolved in dichloromethane (1 mL) then cooled to 0° C. Trifluoroacetic acid (0.5 mL, 6.5 mmol) was added drop-wise then the reaction mixture was warmed to 25° C. After 2 h, the mixture was cooled in an ice bath and neutralized with sodium bicarbonate solution. The mixture was extracted with ethyl acetate, and the combined organic layers washed with brine, dried (sodium sulfate), filtered, and concentrated in vacuo. Purification by chromatography (silica, 0 to 100% of a 0.1:0.01 solution of methanol:NH4OH in dichloromethane) gave 6-((1R,2S)-2-amino-cyclohexylamino)-4-(1-methyl-1H-pyrrolo[2,3-b]pyridin-6-ylamino)-pyridazine-3-carboxylic acid amide (5.8 mg, 32%) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.74-11.82 (m, 1H) 8.35-8.44 (m, 1H) 8.14 (s, 1H) 7.90 (d, J=8.3 Hz, 1H) 7.60-7.67 (m, 1H) 7.32 (d, J=3.3 Hz, 1H) 6.80 (d, J=7.6 Hz, 1H) 6.66 (d, J=8.3 Hz, 1H) 6.40 (d, J=3.3 Hz, 1H) 3.86 (s, 3H) 3.11-3.17 (m, 1H) 1.50-1.75 (m, 8H) 1.23-1.36 (m, 3H); LCMS (EI/CI) m/z: 381 [M+H].

Provenance & Evidence