Ammonium Chloride → HCID 178424478, compound

Participants

Reaction Steps

To a solution of 4-cyano-1H-imidazole-2-carboxylic acid [4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in Example 1, step (g), 120 mg, 0.300 mmol) in 4 mL of THF at −78° C. under Ar was added isopropylmagnesium chloride (165 μL, 0.331 mmol, 2.0 M in THF). The resulting mixture was warmed to RT and stirred for 5 min, cooled to −78° C. again. To the mixture was added tert-butyllithium (530 μL, 0.902 mmol, 1.7 M in pentane) and the resulting mixture was stirred at −78° C. for 10 min. A solution of tetrahydro-thiopyran-4-one (175 mg, 1.50 mmol) in 1 mL of THF was then added, and the reaction was warmed to RT and stirred for 0.5 h under Ar. The mixture was treated with 2 mL of saturated NH4Cl followed by 20 mL of EtOAc, washed with brine (10 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (1-2% MeOH/DCM) gave 85.0 mg (65%) of the title compound as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 12.62 (s, 1H), 9.72 (s, 1H), 8.32 (d, 1H, J=8.6 Hz), 7.74 (d, 1H, J=2.3 Hz), 7.42 (dd, 1H, J=8.6, 2.3 Hz), 7.33 (d, 1H, J=2.3 Hz), 5.78 (m, 1H), 3.12-3.33 (br s, 2H), 2.46-2.54 (m, 2H), 2.26-2.33 (m, 2H), 2.16-2.22 (m, 2H), 2.00-2.13 (m, 4H), 1.79 (s, 1H), 1.59 (t, 2H, J=6.3 Hz), 1.10 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C24H28N4O2S, 437.2 (M+H). found 437.2.

Provenance & Evidence