Dimethylamine → HCID 57537636, compound

Participants

Reaction Conditions

Reaction Steps

2-{5-[4-Chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-2-hydroxy-N,N-dimethyl-acetamide (18 mg, 0.317 mmol) was dissolved in a solution of dimethyl amine (2 mL, 17.7 mmol) and 1,4 dioxane (1 mL). The mixture was heated for at 150° C. for 15 hours in a sealed vessel and concentrated under in vacuo. To the residue were added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (14.5 mg, 0.0381 mmol), dimethylamine hydrochloride salt (12 mg, 0.147 mmol), N,N-dimethylformaldehyde and N,N-Diisopropylethylamine (33 μL, 0.317 mmol). After stirring at 23° C. for 1 hour, the mixture was concentrated. The crude product was dissolved in 1 mL TFA and stirred at 23° C. for 1 hour. The solvent was evaporated and the resulting oil was dissolved in 1 mL DMSO and 50 μL ethylenediamine and purified by mass triggered reverse phase HPLC to afford 2-{5-[4-Dimethylamino-3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-2-hydroxy-N,N-dimethyl-acetamide (1.60 mg, 0.00359 mmol, 1.1% yield). 1H-NMR [500 MHz, d6-DMSO] δ: 8.56 (d, 2H), 7.99 (s, 1H), 7.63 (s, 1H), 7.32 (m, 1H), 7.24 (dd, 1H), 7.04 (d, 1H), 6.97 (t, 1H), 5.57 (s, 1H) 3.68 (s, 4H), 2.95 (s, 4H), 2.82 (s, 3H), 2.18 (s, 6H); MS [MH+] m/z: 446.

Provenance & Evidence