Triethylamine → HCID 56967198, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the product of Example 1, Step 1 (136 mg, 0.524 mmol) in NMP (0.262 mL), in a microwave vial, was added Et3N (0.073 mL, 0.52 mmol) and 4-chloro-1H-pyrrolo[2,3-b]pyridine (16 mg, 0.11 mmol). The resulting solution was heated at 160° C. for 2 hours in a Biotage Initiator microwave. An additional 4 equivalents of 4-chloro-1H-pyrrolo[2,3-b]pyridine (64 mg, 0.42 mmol) was added to the reaction mixture and the resulting solution was stirred at 160° C. for another 2 hours in a Biotage Initiator microwave. The reaction mixture was cooled to ambient temperature and partitioned between EtOAc (50 mL) and saturated sodium bicarbonate (50 mL). The layers were separated, and the organic layer was collected, dried over sodium sulfate and concentrated in vacuo to afford a crude oil that was purified by reverse phase HPLC. Lyophilization of the product fractions afforded the title compound (TFA salt) as a white solid. LRMS calc'd for C22H25N4O2 [M+H]+, 377; found 377. Jak1 activity: +.

Provenance & Evidence