Triethylamine → HCID 90467010, compound

Participants

Reaction Steps

To a stirred solution of 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-amine (25d) (0.1 g, 0.37 mmol) in dichloromethane (10 mL) were added triethylamine (0.15 mL, 1.11 mmol), T3P (0.35 g, 1.11 mmol) and 2-cyclopropylacetic acid (0.037 g, 0.37 mmol and the mixture was stirred for 16 h at room temperature. Then the reaction mixture was poured into water (20 mL) and extracted with dichloromethane (2×50 mL). The combined organic layer was washed with brine and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using 50% ethylacetate in hexane to afford 2-cyclopropyl-N-(1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)acetamide as off-white solid; yield: 25 mg (19%). ES+MS m/z: 352 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.25 (s, 3H), 3.67-3.69 (m, 1H), 3.73-3.76 (m, 1H), 4.50-4.52 (m, 1H), 4.62-4.64 (m, 1H), 5.49 (s, 2H), 6.94-6.96 (m, 3H), 7.27-7.30 (m, 1H), 8.08 (d, J=8.2 Hz), 8.45 (s, 1H), 8.50 (d, J=3.88 Hz), 8.92 (t, J=5.6 Hz).

Provenance & Evidence