Potassium Carbonate → Formate

Participants

Reaction Conditions

Reaction Steps

2-(Boc-amino)-ethylbromide (66 mg, 285 μmol) was added to a suspension of 2-ethyl-4-(5-{3-[(ethyl-methyl-amino)-methyl]-5-methyl-phenyl}-[1,2,4]oxadiazol-3-yl)-6-methyl-phenol (52 mg, 142 μmol) and K2CO3 (60 mg, 427 μmol) in acetonitrile (2 mL). The mixture was stirred at 70° C. for 16 h before it was filtered. The filtrate was concentrated, dissolved in DCM (1 mL) and TFA (1 mL) and stirred at rt for 10 min. The mixture was again concentrated in vacuo and the crude product was purified by prep. HPLC to give the title compound as a formate salt in the form of a white lyophilisate (40 mg). LC-MS: tR=0.47 min; [M+1]+=409.30; 1H NMR (D6-DMSO): δ 1.06 (t, J=7.0 Hz, 3H), 1.26 (t, J=7.5 Hz, 3H), 2.16 (s, 3H), 2.38 (s, 3H), 2.43-2.48 (m, 5H), 2.75 (q, J=7.5 Hz, 2H), 3.26 (t, J=5.0 Hz, 2H), 3.56 (s, 2H), 3.99 (t, J=5.0 Hz, 2H), 7.48 (s, 1H), 7.83 (s, 2H), 7.91 (s, 1H), 7.93 (s, 1H), 8.17 (s, 2H, formate).

Provenance & Evidence