HCID 67528395, compound → HCID 67528662, compound

HRID 219946Notes

Reaction equation

HRID 219946 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([F:24])[CH:15]=3)[N:10]=2)=[CH:5][C:4]=1[N+:25]([O-])=O>CCO.C([O-])(O)=O.[Na+]>[NH2:25][C:4]1[CH:5]=[C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([F:24])[CH:15]=3)[N:10]=2)[CH:7]=[CH:8][C:3]=1[N:2]([CH3:1])[CH3:28]

Participants

4

Reactant 1

HCID 67528395HCID 67528395, compound

Product 1

HCID 67528662HCID 67528662, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of methyl 4-{5-[4-(dimethylamino)-3-nitrophenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate obtained in step 1 (150 mg; 0.39 mmol) in EtOH (15 mL) was added stannous chloride dihydrate (438.05 mg; 1.94 mmol) and stirred at 70° C. for 3 h, then at RT for 16 h. After this time, the solution was diluted with a saturated aqueous solution of NaHCO3 (75 mL) and extracted with EtOAc (100 mL). The combined organic layers were washed with brine (50 mL), dried over magnesium sulfate and concentrated under vacuum to give the title compound. LC/MS (Method B): 357.3 (M+H)+. HPLC (Method A) Rt. 3.75 min (purity: 95.4%).

Workup

  1. waitat RT for 16 h
  2. extractionextracted with EtOAc (100 mL)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-017811749e784fdab4e61cbaee945248
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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