Diethylamine → HCID 86753450, compound

Participants

Reaction Steps

A mixture of 846 mg (1.38 mmol) of 3-[2-[benzyloxycarbonyl-[4-(pyridin-4-yl)butyl]amino]ethyl]-2-(3,5-dirnethylphenyl)-1H-indole-5-carboxylic acid hydrochloride, 862 mg (1.66 mmol) of benzotriazol-1-yloxy-tris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP), and 8.5 mL of dry methylene chloride was treated with 1.16 mL (839 mg; 8.29 mmol) of triethylamine, followed after a few minutes by 0.715 mL (505 mg, 6.91 mmol) of diethylamine. The resulting solution was stirred under nitrogen at room temperature overnight and then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient elution with 1-5% methanol in methylene chloride) afforded a quantitative yield of the desired product; homogeneous by TLC in 95:5 CH2Cl2 -MeOH. 500 MHz 1H NMR (CDCl3) was complex, owing to rotamers, but was consistent with the assigned structure. Mass spectrum (ESI): m/e=631.5 (M+H).

Provenance & Evidence