Water → HCID 49819563, compound

HRID 661281Notes

Reaction equation

HRID 661281 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].Cl[C:7]1[N:11]=[C:10]([CH:12]2[CH2:17][CH:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[CH2:15][N:14]([C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:29])[CH2:13]2)[O:9][N:8]=1.O>O1CCOCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:7]1[N:11]=[C:10]([CH:12]2[CH2:17][CH:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:20][CH:19]=3)[CH2:15][N:14]([C:28]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)=[O:29])[CH2:13]2)[O:9][N:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80192-MethoxyethanolHCID 58116540{3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

Product 1

HCID 49819563HCID 49819563, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 684 mg (8.99 mmol) of ethylene glycol monomethyl ether in 8.00 ml of 1,4-dioxane were added, at RT, 4 Å molecular sieve and 0.90 ml (0.90 mmol; 1 M solution in n-hexane) of phosphazene P4 base. Subsequently, 200 mg (0.450 mmol) of the oxadiazole from Example 23A in 2.0 ml of 1,4-dioxane were added and the reaction mixture was stirred at RT for 2 h. The reaction mixture was admixed with water, filtered and extracted with dichloromethane. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by means of preparative HPLC. Yield: 89.8 mg (41% of theory).

Workup

  1. filtrationfiltered
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-0cec4b3917d5496eb95f5f31c208be9d
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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