Potassium Carbonate → HCID 66932107, compound

Participants

Reaction Conditions

Reaction Steps

4-bromobutyl acetate (186 mg, 936 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 (114 mg, 312 μmol) and K2CO3 (129 mg, 936 μmol) in acetonitrile (2 mL). The mixture was stirred at 70° C. for 2 h before it was filtered. The filtrate was diluted with 25% aq. ammonia (0.5 mL) and a 32% aq. NaOH solution (300 μL) and the bi-phasic mixture was stirred at 70° C. for 2 h. The aq. phase was separated and 1N aq. NaOH (0.4 mL) was added. The now homogenous mixture was separated by prep. HPLC (XBridge 30×75 mm, eluting with a gradient of MeCN in water containing 0.5% of sat. aq. ammonia) to give the title compound as a white lyophilisate (53 mg). LC-MS: tR=0.65 min; [M+1]+=438.25; 1H NMR (D6-DMSO): δ 1.06 (t, J=7.0 Hz, 3H), 1.23 (t, J=7.5 Hz, 3H), 1.61-1.69 (m, 2H), 1.78-1.86 (m, 2H), 2.15 (s, 3H), 2.34 (s, 3H), 2.41-2.48 (m, 5H), 2.71 (q, J=7.5 Hz, 2H), 3.47-3.53 (m, 2H), 3.55 (s, 2H), 3.81-3.86 (m, 2H), 4.47 (br s, 1H), 7.47 (s, 1H), 7.80 (s, 2H), 7.90 (s, 1H), 7.93 (s, 1H).

Provenance & Evidence