Trifluoroacetic acid → 3-(5-(2-(2-(4-Methylphenyl)-5-methyloxazol-4-yl)ethoxy)-3,4-dihydronaphthalen-1-yl)propanenitrile

HRID 1353152Notes

Reaction equation

HRID 1353152 reaction equation
O1CCOCC1.[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]([CH3:37])=[C:17]([CH2:19][CH2:20][O:21][C:22]3[CH:31]=[CH:30][CH:29]=[C:28]4[C:23]=3[CH2:24][CH2:25][CH:26]=[C:27]4[CH2:32][CH2:33][C:34]([NH2:36])=O)[N:18]=2)=[CH:10][CH:9]=1.FC(F)(F)C(O)=O>N1C=CC=CC=1>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[O:15][C:16]([CH3:37])=[C:17]([CH2:19][CH2:20][O:21][C:22]3[CH:31]=[CH:30][CH:29]=[C:28]4[C:23]=3[CH2:24][CH2:25][CH:26]=[C:27]4[CH2:32][CH2:33][C:34]#[N:36])[N:18]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 312751,4-DioxaneHCID 102020143-(5-(2-(2-(4-Methylphenyl)-5-methyloxazol-4-yl)ethoxy)-3,4-dihydronaphthalen-1-yl)propanamide

Product 1

HCID 231579983-(5-(2-(2-(4-Methylphenyl)-5-methyloxazol-4-yl)ethoxy)-3,4-dihydronaphthalen-1-yl)propanenitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a dioxane (15 ml) solution of the compound prepared in Example 10, pyridine (363 μl) and trifluoroacetic acid (423 μl) were added, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate. The diluted solution was washed with 1 N hydrochloric acid, water and a saturated saline in this order, dried with anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to thereby obtain the title compound (533 mg) having the following physical data.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washThe diluted solution was washed with 1 N hydrochloric acid, water
  4. dry with materiala saturated saline in this order, dried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-3de87f195f744a85ab0f7aa8daebef8f
Source dataset
uspto-grants-2007_05
Patent number
US07220864B2

Reaction notes

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