Triacetoxyperiodinane → 2-[2-(3-oxo-cyclobutyl)-1,3-benzothiazol-6-yl]-2H-pyridazin-3-one

HRID 2047537Notes

Reaction equation

HRID 2047537 reaction equation
[OH:1][CH:2]1[CH2:5][CH:4]([C:6]2[S:7][C:8]3[CH:14]=[C:13]([N:15]4[C:20](=[O:21])[CH:19]=[CH:18][CH:17]=[N:16]4)[CH:12]=[CH:11][C:9]=3[N:10]=2)[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.O>[O:1]=[C:2]1[CH2:5][CH:4]([C:6]2[S:7][C:8]3[CH:14]=[C:13]([N:15]4[C:20](=[O:21])[CH:19]=[CH:18][CH:17]=[N:16]4)[CH:12]=[CH:11][C:9]=3[N:10]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 671454642-[2-(3-hydroxy-cyclobutyl)-1,3-benzothiazol-6-yl]-2H-pyridazin-3-one

Product 1

HCID 671458792-[2-(3-oxo-cyclobutyl)-1,3-benzothiazol-6-yl]-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The product of Example 48C (1.63 g, 5.45 mmole) was dissolved in 50 ml anhydrous dichloromethane. Dess-Martin periodinane (3.0 g, 7.07 mmole, [87413-09-0]) was added. After 3 hours at room temperature, the mixture was diluted with water and extracted three times with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide the crude product which was purified by column chromatography (0.25% ammonium hydroxide and 2.5% methanol in dichloromethane) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 8.20 (d, J=2.03 Hz, 1H) 8.07 (d, J=8.82 Hz, 1H) 7.94 (dd, J=3.73, 1.70 Hz, 1H) 7.75 (dd, J=8.82, 2.37 Hz, 1H) 7.26-7.31 (m, 1H) 7.09 (dd, J=9.49, 1.70 Hz, 1H) 4.01-4.15 (m, 1H) 3.54-3.79 (m, 5H). MS: (M+H)+=298.

Workup

  1. extractionextracted three times with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto provide the crude product which
  7. customwas purified by column chromatography (0.25% ammonium hydroxide and 2.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9a2dba7f807b4ba7aef4d52bdf27e3cf
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

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