p-Toluenesulfonic acid monohydrate → HCID 78324585, compound

Participants

Reaction Steps

To a solution of N-benzyl-2-(5-(2,2-dimethyl-1,3-dioxan-5-yl)pyridin-3-yl)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine (60.0 mg, 0.122 mmol) in methanol (15 mL) was added p-toluenesulfonic acid monohydrate (12.0 mg, 0.0610 mmol) and stirred at ambient temperature for 2 h. Reaction mixture was diluted with saturated sodium bicarbonate solution (50 mL) and extracted into DCM (2×50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The resulting residue was purified by preparative HPLC (Condition B-73 as described in general methods) to get 2-(5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)propane-1,3-diol (35.0 mg, 63.5%). LCMS Condition B-12: retention time 2.00, [M+1]=452.2. HPLC Condition B-4: retention time 7.22, purity 97.89%. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.93-2.96 (m, 1H), 3.68-3.77 (m, 4H), 4.69 (br s, 2H), 4.80 (d, J=5.6 Hz, 2H), 6.69 (t, J=5.6 Hz, 1H), 6.79 (d, J=2.8 Hz, 1H), 7.23-7.27 (m, 1H), 7.32-7.41 (m, 5H), 7.46-7.55 (m, 4H), 7.90 (d, J=2.8 Hz, 1H), 8.36 (t, J=2.4 Hz, 1H), 8.51 (d, J=2.0 Hz, 1H), 9.19 (d, J=2.0 Hz, 1H).

Provenance & Evidence