Trifluoroacetic acid → 3-Chloro-4-hydroxybenzoic Acid {4-[2-(4-Benzylpiperazin-1-yl)ethoxy]-2-methoxybenzylidene}hydrazide

HRID 1166770Notes

Reaction equation

HRID 1166770 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:7][NH2:8])=[O:6].Br[CH2:14][CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[C:19]([O:25][CH3:26])[CH:18]=1.[CH2:27]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.FC(F)(F)C(O)=O>CC(O)C>[CH2:27]([N:34]1[CH2:39][CH2:38][N:37]([CH2:14][CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[N:8][NH:7][C:5](=[O:6])[C:4]3[CH:9]=[CH:10][C:11]([OH:12])=[C:2]([Cl:1])[CH:3]=3)=[C:19]([O:25][CH3:26])[CH:18]=2)[CH2:36][CH2:35]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 759941-BenzylpiperazineHCID 109542683-Chloro-4-hydroxybenzohydrazideHCID 229991114-(2-Bromoethoxy)-2-methoxybenzaldehyde

Product 1

HCID 570134633-Chloro-4-hydroxybenzoic Acid {4-[2-(4-Benzylpiperazin-1-yl)ethoxy]-2-methoxybenzylidene}hydrazide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

This compound was prepared analogously to the compound described in the previous example starting from resin bound 3-chloro-4-hydroxybenzoic acid hydrazide (resin—[building block 1]) (2 g, ˜2 mmoles), 4-(2-bromoethoxy)-2-methoxybenzaldehyde ([building block 2]) (0.73 g, 1.5 equivs.), and 1-benzylpiperazine ([building block 3]) (3.3 g, 10 equivs.). After cleavage with 50% trifluoroacetic acid, the residue (1.4 g) was dissolved in 2-propanol (50 ml) and concentrated to 20 ml. The mixture was allowed to stand at 5° C. for 1 h and filtered. The mother liquor was concentrated in vacuo and the residue was purified by column chromatography on silica gel (20 g) eluting with a mixture of methanol and dichloromethane (1:9). This afforded 0.98 g of the title compound.

Workup

  1. customThis compound was prepared analogously to the compound
  2. concentrationconcentrated to 20 ml
  3. filtrationfiltered
  4. concentrationThe mother liquor was concentrated in vacuo
  5. customthe residue was purified by column chromatography on silica gel (20 g)
  6. washeluting with a mixture of methanol and dichloromethane (1:9)

Sources & evidence

ORD record
ord-f81b9bc4b810495b8e01a6fe35bfac2e
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

Loading…