N,N-Dimethylethylenediamine → HCID 69296282, compound

Participants

Reaction Steps

A solution 1-(3-cyclopentyl-1-methyl-1H-pyrazol-5-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea from Example 122 (80 mg, 0.15 mmol) in THF (1 mL) was treated with N,N-dimethylethylenediamine (0.080 mL, 0.74 mmol). The reaction was stirred 1 h at RT, diluted with EtOAc (15 mL) and washed with 2 M aq Na2CO3 (2×10 mL), water (10 mL) and brine (10 mL). The organics were dried (Na2SO4), concentrated in vacuo and chromatographed on reverse phase silica gel to provide 1-(3-cyclopentyl-1-methyl-1H-pyrazol-5-yl)-3-(5-(2-(2-(dimethylamino)ethylamino)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluoro-4-methylphenyl)urea (33 mg, 39% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.87 (s, 1H), 8.72 (d, J=2.0 Hz, 1H), 8.65 and 8.60 (br s, 1H), 7.91 (d, J=8.6 Hz, 1H), 7.75 and 7.59 (m, 1H), 7.66 (s, 1H), 7.14 (d, J=8.4 Hz, 1H), 5.98 (s, 1H), 3.59-3.43 (m, 8H), 2.86 (m, 1H), 2.21 (br s, 6H), 2.49 (m, 2H obscured by solvent), 2.06 (s, 3H), 1.87 (m, 2H), 1.66-1.48 (m, 6H); MS (ESI) m/z: 562.3 (M+H+).

Provenance & Evidence