Diisopropylethylamine → 1-[4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridin-1-yl]-3-piperidin-1-ylpropan-1-one

Participants

Reaction Steps

Alternative preparation: To a suspension/solution of 4-chloro-6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine bis-hydrochloride (495.4 mg, 1.610 mmol, 1 eq), 1-piperidinepropanoic acid (335.4 mg, 2.133 mmol, 1.3 eq), and TBTU (624.4 mg, 1.945 mmol, 1.2 eq) in anhydrous DMF (15 mL), DiPEA (1.4 mL, 8 mmol, 5 eq) was added at rt, under N2, and stirred for 2 h. The solvent was evaporated under reduced pressure. The crude material was adsorbed onto Hydromatrix, dry loaded, and purified by chromatography on silica gel [Jones Flashmaster, 50 g/150 mL cartridge, eluting with MeOH:DCM 2%→5%→10%→7N NH3/MeOH:DCM 2%→5%]. Fractions containing product were combined and concentrated in vacuo, affording the title compound as a yellow solid.

Provenance & Evidence