Hydrochloric Acid → HCID 67106369, compound

HRID 1040408Notes

Reaction equation

HRID 1040408 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1/[CH:21]=[CH:22]/[C:23](=[O:36])[CH2:24][C:25](=[O:35])/[CH:26]=[CH:27]/[C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1.[ClH:37]>C(OCC)(=O)C>[ClH:37].[ClH:37].[Br:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[CH:5]=[CH:4][C:3]=1/[CH:21]=[CH:22]/[C:23](=[O:36])[CH2:24][C:25](=[O:35])/[CH:26]=[CH:27]/[C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 44538649HCID 44538649, compound

Product 1

HCID 67106369HCID 67106369, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1E,6E)-1-[2-bromo-4-(4-tert-butoxycarbonylpiperazin-1-yl)phenyl]-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione (35 mg, 0.063 mmol, synthesized in Example 126) in 1.0 mL of ethyl acetate was added 3M HCl (1.0 mL) at room temperature. After being stirred at room temperature overnight, the reaction mixture was concentrated in vacuo. The residue was treated with diethyl ether, and the resulting solid was collected by filtration. The solid was rinsed with ether, and dried under reduced pressure to obtain the title compound as a solid (28.0 mg, 84%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionThe residue was treated with diethyl ether
  3. filtrationthe resulting solid was collected by filtration
  4. washThe solid was rinsed with ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-cc844740cd9347159ac8371bf9bc2684
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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