Hydrochloric Acid → HCID 15858886, compound

HRID 394689Notes

Reaction equation

HRID 394689 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([CH2:19][NH2:20])=[CH:6]2.[C:21](OC(=O)C)(=[O:23])[CH3:22].Cl>N1C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])=[CH:6]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 18177426HCID 18177426, compound

Product 1

HCID 15858886HCID 15858886, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.42 g (1.57 mmol) of the amine obtained in Step C in 5 ml of anhydrous pyridine is cooled to 0° C.; 0.18 ml (1.97 mmol) of acetic anhydride is then added to the medium. After 30 minutes of stirring under argon, the medium is diluted with dichloromethane and then adjusted to an acid pH with a 1N hydrochloric acid solution. The aqueous phase is extracted with dichloromethane; the organic phase is then washed with a saturated solution of sodium hydrogen carbonate. The residue obtained, after evaporation of the solvent in vacuo, is purified on a silica column (eluant: AcOEt/PE: 70/30) to yield the title amide in the form of a white solid.

Workup

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. washthe organic phase is then washed with a saturated solution of sodium hydrogen carbonate
  3. customThe residue obtained
  4. customafter evaporation of the solvent in vacuo
  5. customis purified on a silica column (eluant: AcOEt/PE: 70/30)

Sources & evidence

ORD record
ord-1e65257f10e7415b93f36f6b2610c25b
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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