Hydrochloric Acid → HCID 86724075, compound

Participants

Reaction Steps

To a solution of methyl 2-[4-(2,4-dichlorophenyl)-1-methyl-7-oxo-3-(2-pyridyl)-4H-pyrazolo[3,4-e][1,4]thiazepin-8-yl]acetate (1.18 g, 2.5 mmol, Preparation #9) in anhydrous THF (50 mL) was added a solution of borane THF complex (9.90 mL, 1M in THF, 4 mmol, Acros), the resulting mixture was stirred at rt for about 16 h and then for about 4 h at about 50° C. After cooling to about 4° C., 6 M aqueous HCl (10 mL) was added dropwise and the mixture stirred for about 45 min at rt. Subsequently, the mixture was cooled again to about 4° C., treated with 2 M aqueous NaOH (35 mL) and extracted with ethyl acetate (75 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, ethyl acetate/DCM 1:1 and ethyl acetate) to give methyl 2-[4-(2,4-dichlorophenyl)-1-methyl-3-(2-pyridyl)-6,7-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepin-8-yl]acetate (0.65 g, 1.4 mmol, 56%) as a white foam, which was used as such: LC-MS (Table 1, Method d) Rt=2.90 min; m/z 463 (M+H)+

Provenance & Evidence