Boron tribromide → HCID 57725645, compound

Temperature

0 °C

To the solution of (S)—N-(1-cyclohexylethyl)-6-methoxybenzo[d]thiazol-2-amine (3.39 g, 10 mmol) in 30 ml of DCM was added 1 M boron tribromide in DCM (20 ml, 20 mmol) slowly at 0° C. The reaction solution was stirred at 0° C. then at RT for 2 hr. The reaction mixture was concentrated to a solid. To the residual solids add 400 ml of ethyl acetate and 90 ml of water and stir at RT. for 10 minutes. With stirring, carefully add excess solid NaHCO3 until basic. Stir at RT about 1 hour to dissolve the solids. Remove the aqueous layer and extract with 100 ml of ethyl acetate. Combine organic layers and wash with 1×50 ml water, 1×50 ml saturated NaCl solution, dry with sodium sulfate, filter and concentrate under reduced pressure. The resulting solid was purified by silica gel column chromatography, eluted with (30% EtOAc: 70% Hexanes) and concentrated in vacuo to give (S)-2-(1-cyclohexylethylamino)benzo[d]thiazol-6-ol as solid (2.0 grams). ES/MS m/z 277.1 (MH+).

1. concentrationThe reaction mixture was concentrated to a solid
2. additionTo the residual solids add 400 ml of ethyl acetate and 90 ml of water
3. stirringstir at RT
4. waitfor 10 minutes
5. stirringWith stirring
6. stirringStir at RT about 1 hour
7. dissolutionto dissolve the solids
8. customRemove the aqueous layer
9. extractionextract with 100 ml of ethyl acetate
10. washCombine organic layers and wash with 1×50 ml water, 1×50 ml saturated NaCl solution
11. dry with materialdry with sodium sulfate
12. filtrationfilter
13. concentrationconcentrate under reduced pressure
14. customThe resulting solid was purified by silica gel column chromatography
15. washeluted with (30% EtOAc: 70% Hexanes)
16. concentrationconcentrated in vacuo

ORD record

ord-6cf1644107074812a6b89c139bef4c30

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173689B2