2-Amino-2-methyl-1-propanol → 2-(6-chloro-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Participants

Reaction Steps

A mixture of 2-(6-chloro-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (140 mg, 0.446 mmol), 2-amino-2-methylpropan-1-ol (48 mg, 0.536 mmol), EDCI (256 mg, 1.338 mmol), HOBt (181 mg, 1.338 mmol) and DIPEA (173 mg, 1.338 mmol) in dry DMF (5 mL) was stirred for 16 hours at room temperature. Water (5 mL) was added and the formed precipitate was separated by filtration, then 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: 35% acetonitrile/65% water (0.1% trifluoroacetic acid V/V) initially, and then proceed to 50% acetonitrile/50% water (0.1% trifluoroacetic acid V/V) in a linear fashion after just 9 min) to afford 2-(6-chloro-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (6 mg, 3%) as a white solid. LCMS: (M+H)+=385; 1H NMR (300 MHz, DMSO+D2O): δ 9.09 (s, 1H), 8.52 (d, 1H, J=8.4 Hz), 8.31 (s, 1H), 7.72 (s, 1H), 7.25 (d, 1H, J=9.0 Hz), 3.59 (s, 2H), 1.41 (s, 6H).

Provenance & Evidence