Trichloroacetonitrile → HCID 118395293, compound

HRID 590887Notes

Reaction equation

HRID 590887 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([CH:15]=O)=[C:10]([Cl:17])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C([N:22](C(C)C)CC)(C)C.Cl.NO.ClC(Cl)(Cl)C#N>C1COCC1.O>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([C:15]#[N:22])=[C:10]([Cl:17])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 11011TrichloroacetonitrileHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 1183952921589541-54-7

Product 1

HCID 118395293HCID 118395293, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound tert-butyl(4,6-dichloro-5-formylpyridin-2-yl)carbamate (3.0 g, 10.3 mmol) in THF (30.0 mL) was added diisopropylethylamine (2.76 mL, 15.4 mmol) followed by hydroxylamine hydrochloride (0.78 g, 11.3 mmol) at 0° C. and was stirred at room temperature for 3 h. After confirming the completion of starting material by TLC, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure to get crude product. To the crude product was added trichloroacetonitrile (30.0 mL) and was heated at 85° C. for 2 h. After confirming the completion of starting material by TLC, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography (hexanes:ethyl acetate=9:1) to afford product. 1H NMR (ppm, 400 MHz, DMSO-d6): δ 11.08 (s, 1H), 8.02 (s, 1H), 1.46 (s, 9H), MS ES calc'd. for C11K11C12N3O2 [M+H]+ 288. Found 288.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto get crude product
  7. temperaturewas heated at 85° C. for 2 h
  8. temperaturethe reaction mixture was cooled to room temperature
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (hexanes:ethyl acetate=9:1)
  11. customto afford product

Sources & evidence

ORD record
ord-b8374e270d654aaf9799761f3a7bc7ee
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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