Trifluoroacetic acid → HCID 69297571, compound

Participants

Reaction Steps

To a stirring solution of 1-(3-t-butylisoxazol-5-yl)-3-(2-fluoro-5-(8-methyl-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea from Example 43 (0.125 g, 0.251 mmol, 1.00 eq) in DMF (2.50 ml) at 0° C. was added unsym-dimethylethylenediamine (0.138 ml, 1.25 mmol, 5.00 eq). After 1 h, the completed reaction was diluted with brine (5 ml) and left to stir overnight. The solids were collected by filtration, rinsed well with H2O and dried on the filter to afford crude desired product (76 mg) as a pale pink solid. The crude product was purified by reverse phase chromatography (5-40% MeCN (w/0.1% TFA)/H2O (w/0.1% TFA)) to afford 1-(3-t-butylisoxazol-5-yl)-3-(5-(2-(2-(dimethylamino)ethylamino)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl)urea (37.3 mg, 0.059 mmol) as the TFA salt following lyophilization. The TFA salt thus obtained was treated with MP-Carbonate resin and certified 0.1N HCl (1.0 eq), frozen and lyophilized to afford the HCl salt. 1H NMR (400 MHz, DMSO-d6): δ 10.44 (s, 1H), 9.56 (brs, 1H), 8.85 (brs, 1H), 8.76 (brs, 1H), 8.41 (dd, J=2.0 and 7.6 Hz, 1H), 8.01 (brs, 1H), 7.95 (s, 1H), 7.37-7.28 (m, 2H), 6.05 (s, 1H), 3.73 (m, 2H), 3.58 (brs, 3H), 3.41 (brs, 2H), 2.85 (brs, 6H), 1.24 (s, 9H); MS (ESI) m/z: 523.2 (M+H+).

Provenance & Evidence