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

HRID 1166770ノート

反応式

HRID 1166770 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f81b9bc4b810495b8e01a6fe35bfac2e
出典データセット
uspto-grants-2003_09
特許番号
US06613942B1

反応ノート

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