Trifluoroacetic acid → HCID 59287379, compound

HRID 1927255Notes

Reaction equation

HRID 1927255 reaction equation
C(O)(C(F)(F)F)=O.C([O:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][C:21]2[O:25][N:24]=[C:23]([C:26]3[C:27]([NH2:32])=[N:28][CH:29]=[CH:30][CH:31]=3)[N:22]=2)=[CH:18][CH:17]=1)C1C=CC=CC=1.C1(SC)C=CC=CC=1.C(=O)([O-])O.[Na+]>O>[NH2:32][C:27]1[C:26]([C:23]2[N:22]=[C:21]([CH2:20][C:19]3[CH:18]=[CH:17][C:16]([OH:15])=[CH:34][CH:33]=3)[O:25][N:24]=2)=[CH:31][CH:30]=[CH:29][N:28]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 516892Sodium BicarbonateHCID 24883025HCID 24883025, compound

Product 1

HCID 59287379HCID 59287379, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of TFA (2 mL) of 3-(5-(4-benzyloxy-benzyl)-[1,2,4]-oxadiazol-3-yl)-pyridin-2-ylamine (52 mg) described in Example 13 was added thioanisole (68 μL) at 0° C., which was stirred for 2 hours and 40 minutes at room temperature. Sodium hydrogencarbonate and water were added at 0° C. to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and filtered, after which the solvent was evaporated from the filtrate under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1) to obtain the titled compound (40 mg).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customafter which the solvent was evaporated from the filtrate under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1)

Sources & evidence

ORD record
ord-0d7ec370d6b34ea39af2eac60f46b0d9
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

Loading…