Hydrochloric Acid → HCID 15858886, compound

HRID 428195Notes

Reaction equation

HRID 428195 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 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-2e61ac58239c4d2791ea69b418e8e67f
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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