Water → HCID 49821456, compound

HRID 74194Notes

Reaction equation

HRID 74194 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].O.[F:25][C:26]([F:31])([F:30])[C:27](O)=O>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:27]([C:26]([F:31])([F:30])[F:25])=[N:15][C:14]=2[CH:16]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Product 1

HCID 49821456HCID 49821456, compoundYield 55.5%

Procedure

5-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.20 g, 0.646 mmol) in trifluoroacetic acid (7 mL) was heated to reflux for 4.5 hours. The reaction mixture was cooled, water was added, and this was extracted with ethyl acetate. The organic layer was washed with aqueous sodium carbonate solution and water, then dried over magnesium sulfate, and concentrate. The residue was purified by silica gel column chromatography to yield the title compound (139 mg, 55.5% yield) as white crystals.

Workup

  1. temperatureto reflux for 4.5 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthis was extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous sodium carbonate solution and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrate
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-75efa7a730bb48bdb787a8b7d9a78b1a
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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