Hydrogen Bromide → HCID 22479176, compound

HRID 2182628Notes

Reaction equation

HRID 2182628 reaction equation
C(C1[CH:29]=[CH:28][C:6]([CH2:7][C:8]23[CH2:15][CH2:14][CH2:13][N:12]2[C:11](=[O:16])[N:10]([C:17]2[CH:22]=[C:21]([Cl:23])[C:20]([O:24]C)=[C:19]([Cl:26])[CH:18]=2)[C:9]3=[O:27])=[CH:5][CH:4]=1)#N.Br.C[CH2:32][O:33][C:34]([CH3:36])=[O:35]>>[CH3:32][O:33][C:34]([C:36]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]23[CH2:15][CH2:14][CH2:13][N:12]2[C:11](=[O:16])[N:10]([C:17]2[CH:22]=[C:21]([Cl:23])[C:20]([OH:24])=[C:19]([Cl:26])[CH:18]=2)[C:9]3=[O:27])=[CH:28][CH:29]=1)=[O:35]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 22479124HCID 22479124, compound

Product 1

HCID 22479176HCID 22479176, compound

Procedure

A mixture of the compound from Example 139 (20 mg) and aqueous HBr (5 mL) was heated under reflux for 40 minutes. EtOAc was added and the organic layer was separated. The aqueous layer was extracted with EtOAC. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by preparative TLC (EtOAc). The obtained material was dissolved in MeOH (2 mL) and few drops of SOCl2 were added. The reaction mixture was heated under reflux for 1 hour. The residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered and concentrated. The product was purified via preparative TLC. MS m/z 449 (MH+). mp. 105.3° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 minutes
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with EtOAC
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by preparative TLC (EtOAc)
  9. dissolutionThe obtained material was dissolved in MeOH (2 mL)
  10. additionfew drops of SOCl2 were added
  11. temperatureThe reaction mixture was heated
  12. temperatureunder reflux for 1 hour
  13. customThe residue was partitioned between EtOAc and water
  14. dry with materialThe organic layer was dried over Na2SO4
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customThe product was purified via preparative TLC

Sources & evidence

ORD record
ord-497d8ca6faff49d7b2f95e53da832d53
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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