2-Methoxyethylamine → HCID 178495853, compound

Participants

Reaction Steps

To a suspension of 4-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(4-hydroxy-tetrahydro-pyran-4-yl)-phenyl]-amide (as prepared in Example 1, step (h), 50.0 mg, 0.120 mmol) in 1.5 mL of DCM at 0° C. was added SOCl2 (26.0 μL, 0.360 mmol) under Ar. After stirring at RT for 2 h, the mixture was cooled to 0° C. To the reaction was then added 2-methoxyethylamine (104 μL, 1.20 mmol) and the resulting mixture was stirred at 0° C. for 2 h. The mixture was diluted with EtOAc (30 mL) and washed with H2O (2×10 mL) and brine (10 mL). After drying over Na2SO4 and concentrating in vacuo, the residue was purified by silica gel chromatography (1-4% MeOH/DCM) to afford the title compound (36.8 mg, 65%) as a white solid. 1H-NMR (1:5 CD3OD/CDCl3; 400 MHz): δ 8.31 (d, 1H, J=8.6 Hz), 7.70 (s, 1H), 7.30 (dd, 1H, J=8.6, 2.3 Hz), 7.20 (d, 1H, J=2.3 Hz), 5.77 (m, 1H), 3.94 (m, 2H), 3.69 (m, 2H), 3.41 (t, 2H, J=6.1 Hz), 3.28 (s, 3H), 2.38 (t, 2H, J=6.1 Hz), 2.28 (m, 2H), 2.07-2.20 (m, 4H), 1.88 (m, 2H), 1.59 (t, 2H, J=6.3 Hz), 1.10 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C27H35N5O3, 476.3 (M−H). found 476.3.

Provenance & Evidence