Hydrochloric Acid → HCID 15372705, compound

HRID 394682Notes

Reaction equation

HRID 394682 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:9]([CH2:18][NH2:19])[O:8][C:7]=2[CH:20]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].Cl>N1C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:9]([CH2:18][NH:19][C:21](=[O:23])[CH3:22])[O:8][C:7]=2[CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 15372702HCID 15372702, compound

Product 1

HCID 15372705HCID 15372705, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.2 g (0.74 mmol) of the amine obtained in Step C is dissolved in 3 ml of anhydrous pyridine; the solution is then cooled to 0° C. After addition of 0.085 ml (0.89 mmol) of acetic anhydride, the reaction medium is stirred for 1 hour at 0° C. The solution is then diluted with dichloromethane and then acidified with a hydrochloric acid solution (1N). The aqueous phase is extracted with dichloromethane; the organic phase is then dried over magnesium sulphate. After evaporation of the solvent in vacuo, the residue obtained is purified on a silica column (eluant: AcOEt/PE: 60/40) to yield the title amide in the form of a white solid.

Workup

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. dry with materialthe organic phase is then dried over magnesium sulphate
  3. customAfter evaporation of the solvent in vacuo
  4. customthe residue obtained
  5. customis purified on a silica column (eluant: AcOEt/PE: 60/40)

Sources & evidence

ORD record
ord-74a3acd651c148328367501227cc37f0
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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