Diisopropylethylamine → 1-(7-(3-(1-hydroxyethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(pyridin-2-yl)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethane-1,2-dione

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Reaction Steps

To a solution of 2-(7-(3-(1-hydroxyethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (18 mg, 0.054 mmol), 4-(pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (1.53 mg, 0.054 mmol) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (20.93 mg, 0.065 mmol) in DMF (1 mL) was added N,N-diisopropylethylamine (0.095 mL, 0.543 mmol). The mixture was stirred at room temperature for 2 hours, diluted with MeOH and purified by prep. HPLC to give 1-(7-(3-(1-hydroxyethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(pyridin-2-yl)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethane-1,2-dione (17 mg, 0.030 mmol, 54.8% yield). LCMS: m/z 526.2 (M+H)+, 1.54 min (method 8). 1H NMR (500 MHz, MeOD) d ppm 9.17 (s, 1H) 8.99-9.10 (m, 1H) 8.61-8.74 (m, 1H) 8.27-8.32 (m, 1H) 7.92-8.04 (m, 2H) 7.74-7.79 (m, 1H) 7.43-7.53 (m, 1H) 5.09 (q, J=6.41 Hz, 1H) 4.80-5.02 (m, 2H) 3.76-4.02 (m, 5H) 3.24-3.38 (m, 2H) 1.60-1.89 (m, 3H).

Provenance & Evidence