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 ii) (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-6edc85f9e4f941f4ac606445e45255bb

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07838675B2