Diisopropylethylamine → HCID 178488471, compound

Participants

Reaction Steps

To a solution of the intermediate from step A (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), NAN-diisopropylethyl amine (92 μL, 0.53 mmol) amino tetrazole (56 mg, 0.66 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 checked by LC-MS and was found to have not gone to completion. An additional equivalent of amino tetrazole was added followed by Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (51 mg, 0.11 mmol). The reaction was complete in 3 hours. It was diluted with DCM (10 mL) and washed with 1N HCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC (Gilson) to give the title compound. 1H NMR (DMSO, 500 MB): δ 8.04(d, J=8.2 Hz, 2H), 7.8(d, J=8.6 Hz, 2H), 7.7(s, 1H), 7.56(d, J=1.8 Hz, 2H), 7.23(d, J=8.2 Hz, 1H), 7.07(s, 1H), 7.01(d, J=9.0 Hz, 2H), 5.56(s, 2H), 3.79(s, 3H). LC-MS: 3.8 min; (M+H)=520.1.

Provenance & Evidence