Water → 1-(4-(3-(6-amino-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)-3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl)-3-phenylurea

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-(3-amino-3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl)-3-phenylurea in dimethyl acetamide (1 mL) was added 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine (135 mg, 1.0 mmol) and diisopropylethylamine (0.4 mL, 0.30 g, 2.30 mmol). The reaction mixture was stirred at 120° C. for 20 hours. After cooling to room temperature the mixture was poured into water (10 ml) and extracted with ethyl acetate (3×10 ml). The combined organics were dried over sodium sulfate and concentrated to give a residue that was purified by reverse phase chromatography on a preparative LC/UV/MS system using a mass triggered fractionation. Compounds were eluted from the HPLC column (Maccel 120-10-C18 SH 10 μm 20 mmID×50 mm) at 88 ml/min with 5-95 acetonitrile/water gradient using 0.1% TFA as modifier to yield 1-(4-(3-(6-amino-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)-3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl)-3-phenylurea (47.6 mg).

Provenance & Evidence