Methanol → HCID 178424461, compound

Participants

Reaction Steps

To a slurry of 4-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(3-hydroxy-1,5-dimethyl-8-oxa-bicyclo[3.2.1]oct-3-yl)-phenyl]-amide (21 mg, 0.044 mmol, as prepared in Example 93) in 1 mL of DCM at 0° C. was added TMSCN (25 μL, 0.19 mmol) followed by SnCl4 (4 mg, 0.01 mmol) dissolved in 0.08 mL of DCM. The reaction was warmed to room temperature and again treated with 25 μL of TMSCN and then SnCl4 (8 mg, 0.02 mmol) in 0.2 mL of DCM. After the reaction became homogeneous 1 mL of MeOH was added followed by 2 mL of water. The mixture was stirred for 5 min, CHCl3 (5 mL) was added and the layers were separated. The organic layer was dried (Na2SO4) and concentrated in vacuo. Purification of the residue twice by preparative TLC (5% MeOH—CHCl3, then 50% EtOAc-hexanes) afforded the title compound (6 mg, 28%). 1H-NMR (CD3OD; 400 MHz): δ 8.09 (d, 1H, J=8.3 Hz), 7.70 (s, 1H), 7.27-7.23 (m, 1H), 7.16-7.12 (m, 1H), 5.66-5.64 (m, 1H), 2.80-2.56 (m, 4H), 2.22-2.14 (m, 2H), 2.02-1.97 (m, 2H), 1.81-1.77 (m, 4H), 1.51-1.46 (m, 2H), 1.25 (s, 3H), 1.25 (s, 1H), 0.98 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C29H33N5O2 484.2 (M+1). found 484.0.

Provenance & Evidence