Diisopropylethylamine → HCID 57801546, compound

Participants

Reaction Steps

To a solution of the intermediate from example 73 step D (100 mg, 0.22 mmol) in 1:1 DMF/DCM (0.54 mL) was added 1-hydroxy-7-azabenzo-triazole (35 mg, 0.264 mmol), N,N-diisopropylethyl amine (92 μL, 0.53 mmol) β-alanine-t-butyl ester hydrochloride (48 mg, 0.26 mmol) and 1-(3-(Dimethylamino)propyl-3-ethyl carbodiimide hydrochloride (51 mg, 0.26 mmol). The reaction was left stirring at room temperature for 18 hours. The reaction was diluted with DCM, washed with 1N HCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 2:5 ethyl acetate-hexanes to give a colorless oil. LC-MS: 4.5 min; (M+H)=580.2. This material was dissolved in 1:1 TFA/DCM (4 mL) and stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and azeotroped with toluene (1×). The residue was purified by reverse phase HPLC (Gilson) to give the title compound. 1H NMR (DMSO, 500 MHz): δ 8.49 (t, J=5.5 Hz, 1H), 7.88 (d, J=2.1 Hz, 2H), 7.76 (d, J=8.3 Hz, 2H), 7.55 (t, J=1.8 Hz, 1H), 7.39 (d, J=8.7 Hz, 2H), 7.1 (s, 1H), 7.09 (d, J=8.9 Hz, 2H), 7.04 (d, J=9.0 Hz, 2H), 5.47 (s, 2H), 3.79 (s, 3H), 3.45 (q, J=7.1 Hz, 2H), 2.49 (t, J=7.1 Hz, 2H). LC-MS: 3.85 min; (M+H)=524.1.

Provenance & Evidence