Hydrochloric Acid → HCID 15858887, compound

HRID 394690Notes

Reaction equation

HRID 394690 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(N(CC)CC)C.[C:28](Cl)(=[O:32])[CH2:29][CH2:30][CH3:31].Cl>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:28](=[O:32])[CH2:29][CH2:30][CH3:31])=[CH:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 18177426HCID 18177426, compound

Product 1

HCID 15858887HCID 15858887, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.45 g (1.7 mmol) of the amine obtained in Step C of Example 42 in 15 ml of anhydrous dichloromethane is cooled to 0° C.; 0.7 ml (5.1 mmol) of triethylamine and also 0.26 ml (2.55 mmol) of butyryl chloride are then added to the medium. Stirring is maintained for 30 minutes; the reaction mixture is 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 passed over a silica column (eluant: AcOEt/PE: 60/40) to yield the title amide in the form of a white solid.

Workup

  1. temperatureis maintained for 30 minutes
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. washthe organic phase is then washed with a saturated solution of sodium hydrogen carbonate
  4. customThe residue obtained
  5. customafter evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-4c433a08b1af4ae1ac6e5da6001ec188
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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