Dimethyl Sulfoxide → HCID 86618610, compound

HRID 1436427Notes

Reaction equation

HRID 1436427 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[N:12]=1.[NH2:22][OH:23].CS(C)=O>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:20]=[CH:19][C:16]([C:17](=[N:22][OH:23])[NH2:18])=[CH:15][CH:14]=2)[N:12]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 787HydroxylamineHCID 24738462HCID 24738462, compound

Product 1

HCID 86618610HCID 86618610, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile (0.10 mg, 0.33 mmol), prepared in Example 6, was dissolved in tetrahydrofuran (2 mL). A 1M solution of hydroxylamine in dimethyl sulfoxide (1.5 mL, 1.5 mmol) was added and the mixture was stirred for 16 h. The mixture was diluted with ethyl acetate and washed with H2O, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (1% methanol/methylene chloride) afforded the title compound (70 mg, 64%) as a white solid. HRMS: calcd for C15H16N4O3S+H+, 333.10159; found (ESI-FT/MS, [M+H]1+), 333.102; Analytical HPLC: purity 100% at 210-370 nm, 6.9 min; 100% at 292 nm, 6.9 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 mm.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0d015e6fb32f44fea2cca3fa66ae86be
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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