Hydrochloric Acid → HCID 57527216, compound

Temperature

-78 °C

To a solution of lithium bis(trimethylsilyl)amide (1.0 M in THF, 35.3 mL) in THF (60 mL) was added a solution of (R)-2-(2-(sec-butylamino)benzo[d]thiazol-6-yl)acetonitrile (3.74 g, 15.2 mmol) in THF (60 mL) at −78° C. over 40 min. The resulting solution was stirred at −78° C. for 10 min before a solution of methyl 2-fluorobenzoate (2.5 mL, 19.6 mmol) in THF (15 mL) was added over 5 min. The mixture was stirred at −78° C. for 1 hr and then at rt for 3 hr before it was poured into ice-cold water (100 mL). After its pH value was adjusted to 9 with 6 N HCl, the mixture was extracted with AcOEt (3×60 mL). The combined extract was washed with brine and dried over anhydrous MgSO4. The solution was concentrated under vacuum, and the residue was subjected to ISCO (2% MeOH/CH2Cl2) to give a mixture (4.09 g) of the title compound and the starting material in a ratio of 1:1.

1. additionwas added over 5 min
2. extractionthe mixture was extracted with AcOEt (3×60 mL)
3. extractionThe combined extract
4. washwas washed with brine
5. dry with materialdried over anhydrous MgSO4
6. concentrationThe solution was concentrated under vacuum

ORD record

ord-728cebf5012d4d85b8b957d479eb1c6f

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994337B2