Sodium ethoxide → HCID 49819700, compound

HRID 661283Notes

Reaction equation

HRID 661283 reaction equation
Cl[C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])[CH2:8]2)[O:4][N:3]=1.[O-:31][CH2:32][CH3:33].[Na+]>C(O)C>[CH2:32]([O:31][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])[CH2:8]2)[O:4][N:3]=1)[CH3:33]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 58116540{3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

Product 1

HCID 49819700HCID 49819700, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 150 mg (0.337 mmol) of the oxadiazole from Example 23A in 6.25 ml of ethanol were added 229 mg (3.37 mmol) of sodium ethoxide, and then the reaction mixture was stirred at RT for 3 days and at 40° C. for 2 days. The solvent was removed under reduced pressure and the crude product was purified by means of preparative HPLC. Yield: 16.8 mg (11% of theory)

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-c9ee3fd7afa04ec2b2121e9ad52f8c2e
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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