2-Methoxyethylamine → HCID 22346933, compound

Participants

Reaction Steps

A mixture of N1-{4-[4-amino-1-(4-formylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-(trifluoromethyl)benzamide (Intermediate 2) (0.075 g, 0.14 mmol), 2-methoxyethylamine (0.018 g, 0.24 mmol), and sodium triacetoxyborohydride (0.106 g, 0.500 mmol) in dichloroethane (1.4 mL) was shaken at room temperature for 24 h. 1N NaOH (1 mL) was added and the reaction mixture was concentrated, dissolved in DMF (2 mL), filtered through a syringe-tip Acrodisc filter, and purified by preparative RP-HPLC (Rainin C18, 8 μm, 300 Å, 25 cm; 20-80% acetonitrile—0.05 M ammonium acetate over 25 min, 21 mL/min); the fraction eluting from 15.0-16.2 min was collected, concentrated, and lyopholized to afford N1-{4-[4-amino-1-(4-{[(2-methoxyethyl)amino]methyl}phenyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-(trifluoromethyl)benzamide as a white solid (0.010 g, 0.016 mmol): 1H NMR (d6-DMSO, 400 MHz): δH 9.94 (1H, d, J=4.0 Hz), 8.35-8.37 (2H, m), 8.16 (2H, d, J=8.0 Hz), 8.01 (1H, t, J=7.4 Hz), 7.90 (1H, d, J=10.0 Hz), 7.75 (1H, d, J=8.0 Hz), 7.52 (2H, d, J=8.0 Hz), 7.45 (1H, s), 7.40 (1H, d, J=8.8 Hz), 3.96 (3H, s), 3.80 (2H, s), 3.42-3.45 (2H, m), 3.25 (2H, m), and 2.70-2.71 (2H, m); RP-HPLC (Hypersil C18, 5 μm, 100 Å, 15 cm; 5%-100% acetonitrile—0.1 M ammonium acetate over 15 min, 1 mL/min). Rt 10.23 min. MS: MH+610.2.

Provenance & Evidence