Dimethylformamide → HCID 59239322, compound

Participants

Reaction Steps

(S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (71 mg, 0.18 mmol) and N,N-diisopropylethylamine (6.0E1 uL, 0.34 mmol) were dissolved in N,N-Dimethylformamide (1.0 mL, 13 mmol). Oxazole-5-carboxylic acid (30.0 mg, 0.265 mmol) 1-hydroxybenzotriazole (27.8 mg, 0.206 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (49.9 mg, 0.260 mmol) were weighed out into a vial, and the solution of the amines was added, then the reaction stirred overnight. The resultant precipitate was removed by filtration and washed with H2O. The resulting solid was purified by reverse phase HPLC: 1H NMR (400 MHz, DMSO) δ 8.68 (s, 1H), 8.63 (s, 1H), 8.19 (d, J=8.4 Hz, 2H), 7.88 (s, 1H), 7.49 (d, J=8.7 Hz, 2H), 6.18 (t, J=5.5 Hz, 1H), 4.98-4.54 (m, 2H), 4.19-4.07 (m, 1H), 4.00-3.54 (m, 7H), 3.48-3.37 (m, 1H), 3.15-3.08 (m, 2H), 2.92-2.65 (m, 2H), 1.26 (d, J=6.6 Hz, 3H), 1.06 (t, J=7.2 Hz, 3H) LC-MS: m/z=+492.2 (M+H)+.

Provenance & Evidence