Acetic Acid → HCID 136216213, compound

A mixture of 4-(4-bromo-2-methyl-phenyl)-1,7-dimethyl-3-(2-pyridyl)-4,6-dihydropyrazolo[3,4-e][1,4]thiazepine (0.48 g, 1.13 mmol., Preparation J.1), acetic acid (0.194 mL, 3.40 mmol) and Na(AcO)3BH (0.29 g, 1.36 mmol) in DCE (30 mL) was stirred at rt for about 16 h. Additional acetic acid (0.194 mL, 3.4 mmol) and Na(AcO)3BH (0.29 g, 1.36 mmol) were added and stirring was continued for about another 24 h, at rt. The resulting mixture was concentrated in vacuo and partitioned between 5% aq sodium bicarbonate (60 mL) and ethyl acetate (35 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (35 mL). The combined organic layers were washed with water (20 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, ethyl acetate/hexanes 1:1) to give 4-(4-bromo-2-methyl-phenyl)-1,7-dimethyl-3-(2-pyridyl)-4,6,7,8-tetrahydropyrazolo[3,4-e][1,4]thiazepine (0.413 g, 0.96 mmol, 85%) as a pale yellow oil as a racemic mixture of two diastereomers (ratio 63:37). LC-MS (Table 1, Method g) Rt=2.75 and 2.79 min; m/z 429, 431 (M+H)+

1. stirringstirring
2. customwas continued for about another 24 h, at rt
3. concentrationThe resulting mixture was concentrated in vacuo
4. custompartitioned between 5% aq sodium bicarbonate (60 mL) and ethyl acetate (35 mL)
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with ethyl acetate (35 mL)
7. washThe combined organic layers were washed with water (20 mL)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by column chromatography (SiO2, ethyl acetate/hexanes 1:1)

ORD record

ord-5ab654160f5646438a8e3b3313d55858

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150592B2