Lithium bis(trimethylsilyl)amide → HCID 66599789, compound

Participants

Reaction Steps

To a cooled (−78° C.) 1M solution of lithium hexamethyldisilazane (0.88 mL, 0.88 mmol) in THF was added N3,N3-Dimethyl-N1-[3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzoimidazol-5-yl]-pentane-1,3-diamine (82 mg, 0.22 mmol) in 1 mL THF. Solution turned bright orange. After 5 min, the reaction mixture was treated with 3-isoquinolin-4-yl-4-methoxy-benzaldehyde (58 mg, 0.22 mmol) in 1 mL THF. After 20 minutes, the reaction mixture was removed from cold bath, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was then dissolved in DCM: TFA. After 1 hour, the reaction mixture was concentrated and purified by HPLC (Deltapak C18, acetonitrile: 0.1% trifluoroacetic acid), then neutralized using PL-HCO3 SPE to obtain 19 mg [6-(4-dimethylamino-piperidin-1-yl)-1H-benzoimidazol-2-yl]-(3-isoquinolin-4-yl-4-methoxy-phenyl)-methanone in 17% yield. MS m/z 506.5 (M+H)+.

Provenance & Evidence