Triethylamine → HCID 67497850, compound

HRID 74289Notes

Reaction equation

HRID 74289 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.C(N(CC)CC)C.[NH2:27][CH2:28][C:29]([N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)=[O:30].[H][H]>C(#N)C.[C].[Pd].O>[N:31]1([C:29]([CH2:28][NH:27][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[N:12]=3)=[CH:4][C:3]=2[NH2:17])=[O:30])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 12291813HCID 12291813, compoundHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 67497850HCID 67497850, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (1.20 g, 4.6 mmol) in acetonitrile (24 mL) was added triethylamine (1.17 g, 11.6 mmol) and aminoacetylmorpholine (0.73 g, 5.1 mmol), and this was heated to reflux for 3 h. 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 methanol (40 mL) was added 10% palladium-carbon (120 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 (1.50 g, 91% yield) as light brown crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 3 h
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a solution of the residue obtained in methanol (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-f6ff6c81e3c84026b2620a76bff1bddb
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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