Hydrochloric Acid → HCID 10377971, compound

HRID 394686Notes

Reaction equation

HRID 394686 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][C:7]([CH2:13][NH2:14])=[CH:6]2.C(N(CC)CC)C.[C:22](Cl)(=[O:26])[CH2:23][CH2:24][CH3:25].Cl>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][C:7]([CH2:13][NH:14][C:22](=[O:26])[CH2:23][CH2:24][CH3:25])=[CH:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 15391783HCID 15391783, compound

Product 1

HCID 10377971HCID 10377971, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.49 g (2.57 mmol) of the amine obtained in Step B of Example 40 in 10 ml of dichloromethane is cooled to 0° C.; 1 ml (7.7 mmol) of triethylamine and also 0.41 g (3.85 mmol) of butyryl chloride are then added in succession to the medium. After 30 minutes of stirring under an inert atmosphere, the reaction mixture is acidified with a hydrochloric acid solution (1N); the aqueous phase is then extracted with dichloromethane. The organic phase, dried over magnesium sulphate and then filtered, is concentrated in vacuo. Chromatography on a silica column (eluant: PE/AcOEt: 40/60) yields the title amide in the form of a white solid.

Workup

  1. extractionthe aqueous phase is then extracted with dichloromethane
  2. dry with materialThe organic phase, dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-b50a73e33e8f406fb2947a27e8dd311f
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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