Sodium Bicarbonate → Azd-5069

HRID 2388789Notes

Reaction equation

HRID 2388789 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:25][C@@H:26]([C@@H:28]2[CH2:32][O:31]C(C)(C)[O:29]2)[CH3:27])[N:12]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:25][C@H:26]([CH3:27])[C@@H:28]([OH:29])[CH2:32][OH:31])[N:12]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 53628361N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide

Product 1

HCID 56645576Azd-5069

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fe270724e154475ba1db763a630a8e5c
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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