Hydrochloric Acid → HCID 21849908, compound

HRID 617817Notes

Reaction equation

HRID 617817 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[ClH:15].Cl.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]2[C:33]3[C:32]4[C:27]5=[C:28]([C:34](=[O:43])[N:35]([CH2:38][CH2:39][N:40]([CH3:42])[CH3:41])[C:36](=[O:37])[N:26]5[C:25]=3[CH:24]=[CH:23][C:22]=2[CH:44]=1)[CH:29]=[CH:30][CH:31]=4.Cl>ClCCl.C(O)C.CO>[ClH:15].[C:8]([NH:17][C:18]1[CH:19]=[CH:20][C:21]2[C:33]3[C:32]4[C:27]5=[C:28]([C:34](=[O:43])[N:35]([CH2:38][CH2:39][N:40]([CH3:41])[CH3:42])[C:36](=[O:37])[N:26]5[C:25]=3[CH:24]=[CH:23][C:22]=2[CH:44]=1)[CH:29]=[CH:30][CH:31]=4)(=[O:10])[CH3:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69844254HCID 69844254, compound

Product 1

HCID 21849908HCID 21849908, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4 ml of triethylamine and 2 ml of acetic anhydride were successively added to a suspension of 141 mg (0.379 mmol) of the free base of the compound of Example 49 in dichloromethane (20 ml) under stirring at room temperature and stirring was continued for 16 hours. After concentrating, 30 ml of methanol was added to the residue. Next, the obtained mixture was made basic by adding an aqueous solution of sodium hydrogencarbonate thereto. The precipitate was recovered by filtration and washed with water. The solid matter thus obtained was suspended in ethanol and conc. hydrochloric acid was added thereto under stirring at room temperature. After further adding methanol and dichlromethane thereto, stirring was continued. After concentrating, ethanol was added thereto and the obtained mixture was heated under reflux and then brought back to room temperature. The precipitate was recovered by filtration to thereby give 148 mg of the title compound.

Workup

  1. stirringstirring
  2. concentrationAfter concentrating
  3. addition30 ml of methanol was added to the residue
  4. additionby adding an aqueous solution of sodium hydrogencarbonate
  5. filtrationThe precipitate was recovered by filtration
  6. washwashed with water
  7. customThe solid matter thus obtained
  8. stirringunder stirring at room temperature
  9. stirringstirring
  10. concentrationAfter concentrating
  11. additionethanol was added
  12. temperaturethe obtained mixture was heated
  13. temperatureunder reflux
  14. custombrought back to room temperature
  15. filtrationThe precipitate was recovered by filtration

Sources & evidence

ORD record
ord-d5cc7b2bf58841c3b151bc8521ac4f28
Source dataset
uspto-grants-1999_09
Patent number
US05952335

Reaction notes

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