Water → 2-(2-(Tetrahydrofuran-2-yl)methylaminoanilin-5-yl)benzoxazole

HRID 74277

Reaction equation

HRID 74277 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.[NH2:20][CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][O:23]1.O.[H][H]>C(#N)C.[C].[Pd]>[O:23]1[CH2:24][CH2:25][CH2:26][CH:22]1[CH2:21][NH:20][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[NH2:17]

Participants

7

Reactant 4

HCID 962WaterHCID 253298TetrahydrofurfurylamineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674981632-(2-(Tetrahydrofuran-2-yl)methylaminoanilin-5-yl)benzoxazoleYield 86.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (0.40 mg, 1.5 mmol) in acetonitrile (8 mL) was added 2-aminomethyltetrahydrofuran (0.36 g, 3.6 mmol), and this was heated to reflux for 7 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a solution of the residue obtained in a solvent mixture of methanol/tetrahydrofuran=1:1 (40 mL) was added 10% palladium-carbon (40 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 3 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (0.40 g, 84% yield) as a brown syrup.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 7 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a solution of the residue obtained in a solvent mixture of methanol/tetrahydrofuran=1:1 (40 mL)
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-45b518e81f044c6c87c99006ac06f65a
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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