Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[[2-hydroxy-1-(hydroxymethyl)ethyl]thio]-pyrimidin-4-yl]azetidine-1-sulfonamide

HRID 1024866Notes

Reaction equation

HRID 1024866 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]([S:25][CH:26]2[CH2:31][O:30]C(C3C=CC=CC=3)[O:28][CH2:27]2)[N:12]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO.O>[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[CH2:22][CH2:23][CH2:24]2)(=[O:20])=[O:19])[CH:14]=[C:13]([S:25][CH:26]([CH2:27][OH:28])[CH2:31][OH:30])[N:12]=1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 53628349N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[(2-phenyl-1,3-dioxan-5-yl)thio]pyrimidin-4-yl]azetidine-1-sulfonamide

Product 1

HCID 59558829N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[[2-hydroxy-1-(hydroxymethyl)ethyl]thio]-pyrimidin-4-yl]azetidine-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

A solution of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2-phenyl-1,3-dioxan-5-yl)thio]pyrimidin-4-yl]azetidine-1-sulfonamide (the product of step (0.11 g) and pyridinium para-toluenesulfonate (99 mg) in methanol (5 mL) and H2O (2 drops) was heated at 60° C. for 1 h. The solution was cooled and the solvent evaporated under reduced pressure. The residue was dissolved in EtOAc, washed with H2O, dried (MgSO4) and filtered. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel, eluting with EtOAc/iso-hexane (8:2) to give the subtitle product as a yellow gum. The gum was dissolved in DCM and methanol, filtered through charcoal and the filtrate evaporated under reduced pressure. The residual solid was dried under high vacuum at 40° C. to give the title product as a white solid. Yield: 50 mg

Workup

  1. temperatureThe solution was cooled
  2. customthe solvent evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with H2O
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by flash chromatography on silica gel
  9. washeluting with EtOAc/iso-hexane (8:2)

Sources & evidence

ORD record
ord-00cd235331524243a901dce1f123ff3f
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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