Water → HCID 58044466, compound

HRID 1524218Notes

Reaction equation

HRID 1524218 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-846015ce342c4c489d7d3e8cce3e2717
Source dataset
uspto-grants-2015_07
Patent number
US09079901B2

Reaction notes

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