Water → HCID 58044466, compound

HRID 2368028Notes

Reaction equation

HRID 2368028 reaction equation
O[CH:2]([CH3:28])[CH2:3][NH:4][C:5](=[O:27])[CH2:6][N:7]1[C:25](=[O:26])[N:10]2[CH:11]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[CH:13]=[CH:14][C:9]2=[N:8]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>C1COCC1>[CH3:28][C:2]1[O:27][C:5]([CH2:6][N:7]2[C:25](=[O:26])[N:10]3[CH:11]=[C:12]([C:15]4[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=4)[CH:13]=[CH:14][C:9]3=[N:8]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 66631980HCID 66631980, compound

Product 1

HCID 58044466HCID 58044466, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2-Hydroxypropyl)-2-(3-oxo-6-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-2 (3H)-yl)acetamide (30.0 mg, 0.0761 mmol) was treated with Dess-Martin periodinane (64.6 mg, 0.1522 mmol, 2.0 equiv.) in THF (2 mL) at room temperature in a 50 mL round bottomed flask. After stirring for 1 h, water (30 mL) was added and the whole was extracted with EtOAc (30 mL×3). Combined organic layers were washed with sat. Na2S2O3 aq. solution (30 mL), sat. NaHCO3 aq. solution (30 mL) and brine (30 mL) successively. The organic layer was dried over Na2SO4. The solvent was removed under a reduced pressure to give the desired product as colorless crystals (2-(3-oxo-6-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-2 (3H)-yl)-N-(2-oxopropyl)acetamide, 30.3 mg, 0.077 mmol, >99%). LCMS (EI: 70 eV) 415 (M++Na), 393 (M++1).

Workup

  1. extractionthe whole was extracted with EtOAc (30 mL×3)
  2. washCombined organic layers were washed with sat. Na2S2O3 aq. solution (30 mL), sat. NaHCO3 aq. solution (30 mL) and brine (30 mL) successively
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customThe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-2253c655e7f64caeb8e644dce1653e7d
Source dataset
uspto-grants-2014_04
Patent number
US08703759B2

Reaction notes

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