Sodium Bicarbonate → Azd-5069

To a solution of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide (the product of step (0.13 g) in DCM (5 mL) was added iron (III) chloride hexahydrate (0.24 g). The reaction mixture was stirred at ambient temperature for 1 h, then saturated aqueous sodium bicarbonate (10 mL) was added. The layers were separated and the aqueous material extracted with DCM (3×10 mL) and EtOAc (3×10 mL). The combined organic extracts were washed with saturated sodium chloride, dried (MgSO4), filtered and evaporated. The residual pale yellow solid was slowly precipitated from DCM, filtered and the resulting material washed with minimal cold DCM (2×1 mL) to afford the title compound as a white powder. Yield: 45 mg.

1. customThe layers were separated
2. extractionthe aqueous material extracted with DCM (3×10 mL) and EtOAc (3×10 mL)
3. washThe combined organic extracts were washed with saturated sodium chloride
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customevaporated
7. customThe residual pale yellow solid was slowly precipitated from DCM
8. filtrationfiltered
9. washthe resulting material washed with minimal cold DCM (2×1 mL)

ORD record

ord-91b867461b25425c95b52a1997df9565

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410123B2