Hydrochloric Acid → N-tert-butyl-2-(5-isopropyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Steps

To a stirred solution of (7-(tert-butylcarbamoyl)-2-(5-isopropyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate (0.2 g, crude) in dioxane/water (5 mL/10 mL) was added KOH (0.23 g, 4.1 mmol). The mixture was stirred at room temperature for 3 hours. Then the reaction mixture treated with 1N HCl to pH=3-4. The solvent was removed under reduced pressure and the residue triturated with water (15 mL) and dried to give a crude product which was purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; the gradient conditions are: 62% acetonitrile/38% water (0.1% trifluoroacetic acid, v/v) initially, and then proceed to 64% acetonitrile/36% water (0.1% trifluoroacetic acid, v/v) in a linear fashion after just 9 min.) to give N-tert-butyl-2-(5-isopropyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.05 g) as a yellow solid. LCMS: (M+H)+=391; 1H NMR (300 MHz, CD3OD): δ 9.05 (s, 1H), 8.29 (s, 1H), 8.16 (s, 1H), 7.61 (d, 1H, J=8.7 Hz), 7.48 (dd, 1H, J1=8.7 Hz, J2=1.5 Hz), 4.18 (s, 3H), 3.19-3.02 (m, 1H), 1.58 (s, 9H), 1.35 (d, 6H, J=6.6 Hz).

Provenance & Evidence