Triethylamine → HCID 54290741, compound

Participants

Reaction Steps

To a suspension of 3-(5-(1,2,4-triazol-1-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-3-yl)propionic acid (0.108 g) in dry DMF (3 mL) was added 1-benzylpiperazine (0.11 mL, 0.63 mmol), 1-hydroxybenzotriazole (71 mg, 0.52 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (0.1 g, 0.52 mmol) and triethylamine (73 μL, 0.52 mmol) and this mixture was stirred at ambient temperature under nitrogen for 64 hours. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate (25 mL) and water (25 mL). The two phases were separated and the aqueous phase was extracted with ethyl acetate (2×20 mL). The combined organics were dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica eluting with a gradient of 2 to 5% MeOH in DCM, followed by 95:5:1, DCM:MeOH:NH3 to give the title compound (0.126 g, 72%) as a pale yellow foam. 1H NMR (360 MHz, CDCl3) δ 1.88-1.96 (1H, m), 2.07-2.15 (1H, m), 2.30-2.40 (6H, m), 3.28-3.60 (8H, m), 3.72-3.83 (2H, m), 7.19-7.27 (5H, m), 7.57 (1H, s), 7.66 (1H, s), 7.95 (1H, s) and 8.91 (1H, s).

Provenance & Evidence