Ethylamine → HCID 24805173, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3,3-dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbaldehyde (0.133 g, 0.49 mmol) (Example 9a) in dichloroethane (2 mL) is added ethylamine (0.37 mL, 0.738 mmol) and sodium triacetoxyborohydride (0.313 g, 1.477 mmol). The reaction mixture is stirred at 50° C. for 5 h. The mixture is cooled to room temperature, washed with saturated aqueous sodium bicarbonate and is extracted with ethyl acetate. The organic phase is dried over Na2SO4 and concentrated in vacuo. The residue is dissolved in methanol (5 mL) and purified by reverse phase HPLC to give 4-(5-ethylaminomethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one; HRMS (ESI) m/z 300.1705 [(M+H)+: Calcd for C17H22N3O2: 300.1712]; 1H NMR (400 MHz, MeOD) of the TFA salt δ ppm 1.27 (s, 3 H), 1.46 (t, J=6.8 Hz, 3 H), 1.59 (s, 3 H), 3.35-3.40 (m, 2 H), 4.65 (br. s, 2 H), 5.82 (s, 1 H), 7.51 (br. s, 1 H), 7.64 (d, J=7.3 Hz, 1 H), 7.75 (td, J=7.8, 1.0 Hz, 1 H), 7.84 (td, J=7.6, 1.3 Hz, 1 H), 7.92 (br. s, 1 H), 8.30 (dd, J=7.8, 1.3 Hz, 1 H).

Provenance & Evidence