2,2,2-Trifluoroethanol → HCID 58116555, compound

HRID 661285Notes

Reaction equation

HRID 661285 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].Cl[C:8]1[N:12]=[C:11]([CH:13]2[CH2:18][CH:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[CH2:16][N:15]([C:29]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:30])[CH2:14]2)[O:10][N:9]=1>O1CCOCC1>[N:31]1([C:29]([N:15]2[CH2:16][CH:17]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([F:27])([F:28])[F:26])=[CH:23][CH:24]=3)[CH2:18][CH:13]([C:11]3[O:10][N:9]=[C:8]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[N:12]=3)[CH2:14]2)=[O:30])[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 58116540{3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

Product 1

HCID 58116555HCID 58116555, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 112 mg (1.12 mmol) of 2,2,2-trifluoroethanol in 4.00 ml of 1,4-dioxane were added, at RT, 4 Å molecular sieve and 0.23 ml (0.45 mmol; 2 M solution in THF) of phosphazene P4 base. Subsequently, 100 mg (0.225 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 filtered, diluted with dichloromethane and washed with 1 N aqueous hydrogen chloride solution. 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: 12.4 mg (11% of theory)

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with dichloromethane
  3. washwashed with 1 N aqueous hydrogen chloride solution
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-cc8c2f75c5744297b183774582fd6470
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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