Diisopropylethylamine → HCID 58709851, compound

Participants

Reaction Steps

A solution of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (11.5 mg, 0.0343 mmol, 1 eq) and 1-hydroxy-7-azabenzotriazole (HOAt) (5.6 mg, 0.041 mmol, 1.2 eq) in n-butanol (1 mL) was stirred at 80° C. for 15 h. Solid that had formed during the course of the reaction was filtered over a Hirsh funnel and washed with minimal n-butanol. The filtrate was concentrated in vacuo. To a solution of the solid (3-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-3H-[1,2,3]triazolo[4,5-b]pyridine) (6.4 mg, 0.015 mmol, 1 eq) in DMSO (1 mL), di-tert-butyldicarbonate (5.0 mg, 0.023 mmol, 1.5 eq) and DiPEA (20 μL, 0.1 mmol, 7 eq) were added and the reaction was stirred at rt for 2 h. This solution was combined with the concentrated filtrate and purified on the MDPS yielding the title compound. 1H NMR (400 MHz, MeOH-d4): δ=1.51 (s, 9H), 2.64 (s, br, 2H), 3.70 (s, br, 2H), 4.17 (s, br, 2H), 6.46 (s, br, 1H), 6.74 (s, 1H), 7.61 (dd, J=8.4, 4.4 Hz, 1H), 8.13 (s, 1H), 8.61 (d, J=8.0 Hz, 1H), 8.74 (d, J=4.4 Hz, 1H). MS (ES+): m/z 435.00 (62) [MH+]. HPLC: tR=3.36 min (ZQ2000, polar—5 min).

Provenance & Evidence