HCID 66632553, compound → HCID 58044466, compound

HRID 2368029Notes

Reaction equation

HRID 2368029 reaction equation
[O:1]=[C:2]1[N:6]2[CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]1[CH2:21][C:22]([NH:24][CH2:25][C:26](=[O:28])[CH3:27])=O>O=P(Cl)(Cl)Cl>[CH3:27][C:26]1[O:28][C:22]([CH2:21][N:3]2[C:2](=[O:1])[N:6]3[CH:7]=[C:8]([C:11]4[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][CH:12]=4)[CH:9]=[CH:10][C:5]3=[N:4]2)=[N:24][CH:25]=1

Participants

3

Reactant 1

HCID 66632553HCID 66632553, compound

Product 1

HCID 58044466HCID 58044466, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
80 °C

Procedure

2-(3-oxo-6-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-2 (3H)-yl)-N-(2-oxopropyl)acetamide was dissolved in POCl3 (3 mL) in a 50 mL round bottomed flask. The mixture was heated at 70-90° C. for 2 h and then 100° C. for 15 h. After removal of POCl3 under a reduced pressure, obtained residue was quenched with sat. NaHCO3 aq. solution (30 mL). The whole was extracted with EtOAc (30 mL×3). Combined organic layers were washed with brine (30 mL) and dried over Na2SO4. The solvent was removed under a reduced pressure to give compound 172 as pink crystals, 30.3 mg, 0.0756 mmol, >99%). LCMS (EI: 70 eV) 397 (M++Na), 375 (M++1).

Workup

  1. customAfter removal of POCl3 under a reduced pressure
  2. customobtained residue
  3. customwas quenched with sat. NaHCO3 aq. solution (30 mL)
  4. extractionThe whole was extracted with EtOAc (30 mL×3)
  5. washCombined organic layers were washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-b403604d01db42f297cac4f802a43ccb
Source dataset
uspto-grants-2014_04
Patent number
US08703759B2

Reaction notes

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