Hydrochloric Acid → {(8S)-8-Methyl-3-{1-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-8-yl}methanol

The compound (280 mg, 0.55 mmol) obtained in Example 33-1) was dissolved in methanol (3 mL). A 4 N solution (1.37 mL) of hydrochloric acid in dioxane was added to the solution, and the mixture was stirred at room temperature for 1 h. The solvent was distilled off, the residue was dissolved in a mixed solvent of methylene chloride (50 mL) and methanol (2 mL), and the mixture was separated into organic and aqueous layers by the addition of saturated aqueous sodium hydrogencarbonate (10 mL). The organic layer was washed with saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=0% to 50%) to obtain the title compound (175 mg, 81%) in a colorless solid form.

1. distillationThe solvent was distilled off
2. dissolutionthe residue was dissolved in a mixed solvent of methylene chloride (50 mL) and methanol (2 mL)
3. customthe mixture was separated into organic and aqueous layers
4. additionby the addition of saturated aqueous sodium hydrogencarbonate (10 mL)
5. washThe organic layer was washed with saturated sodium chloride solution
6. dry with materialdried with anhydrous magnesium sulfate
7. distillationThe solvent was distilled off under reduced pressure
8. customthe obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=0% to 50%)

ORD record

ord-cbccd51d0356404aaf5f44d075474d49

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927536B2