1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(2-Fluoro-4-iodophenylamino)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ((S)-2-hydroxypropoxy)-amide

Participants

Reaction Steps

To a solution of 4-(2-fluoro-4-iodophenylamino)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (728 mg, 1.4 mmol), HOBt (228 mg, 1.7 mmol) and EDCI (323 mg, 1.7 mmol) in DMF (15 mL) was added a solution of (S)-1-aminooxypropan-2-ol hydrochloride (200 mg, 1.5 mmol), and DIPEA (596 μL, 3.5 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature for 3 hours then diluted with water (30 mL) and the aqueous layer extracted with dichloromethane (3×20 mL). The combined organic extracts were filtered through a hydrophobic frit and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—SPE, gradient 0-100% ethyl acetate in cyclohexane) to yield the title compound as a cream solid (500 mg, 60%). LCMS (Method B): RT=3.23 min, [M+H]+=592.

Provenance & Evidence