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

HRID 1166770노트

반응식

HRID 1166770 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f81b9bc4b810495b8e01a6fe35bfac2e
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613942B1

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