Methyl iodide → HCID 178484790, compound

Participants

Reaction Steps

To a 100 mL round-bottom flask was added tert-butyl (trans)-4-(6-(6-(4-fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)cyclohexylcarbamate (4.00 g, 7.74 mmol; Example # K.1.1.35) and MeI (0.533 mL, 8.52 mmol) which were then dissolved in THF (10 mL). NaH (0.619 g, 15.5 mmol) was added. The reaction was allowed to stir for about 16 h at ambient temperature after which time TFA (5 mL) was added. The reaction was allowed to stir at ambient temperature for about 2 h after which time the reaction was quenched with aqueous NaHCO3 and the organic layer was separated. The aqueous layer was washed with DCM and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography using EtOAc/MeOH (gradient, 1:0 to 9:1) to provide the title compound. (0.032 g, 1.0%): LC/MS (Table 1, Method a) Rt, =1.6 min; MS m/z: 431.2 (M+H)+.

Provenance & Evidence