Trifluoroacetic acid → (Z)-2-[(5-chloro-1H-indol-3-yl)methylene]-6-hydroxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one dihydrochloride

HRID 1749742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749742
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2/[CH:11]=[C:12]1\[O:13][C:14]2[C:21]([CH2:22][N:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)=[C:20]([OH:36])[CH:19]=[CH:18][C:15]=2[C:16]\1=[O:17].FC(F)(F)C(O)=O>C(Cl)Cl>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2/[CH:11]=[C:12]1\[O:13][C:14]2[C:21]([CH2:22][N:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]3)=[C:20]([OH:36])[CH:19]=[CH:18][C:15]=2[C:16]\1=[O:17]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86681936tert-butyl (Z)-4-({2-[(5-chloro-1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate

Produkt 1

HCID 86681937(Z)-2-[(5-chloro-1H-indol-3-yl)methylene]-6-hydroxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one dihydrochlorideAusbeute 273,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (Z)-4-({2-[(5-chloro-1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0710 g, 0.139 mmol) in methylene chloride (3.0 mL) was added with trifluoroacetic acid (3.0 mL), and then the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, then a solution of the resulting residue in methanol (8 mL) was added with a 5% solution of hydrogen chloride in methanol (2 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated to obtain (Z)-2-[(5-chloro-1H-indol-3-yl)methylene]-6-hydroxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one dihydrochloride (0.0611 g, 98%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additiona solution of the resulting residue in methanol (8 mL) was added with a 5% solution of hydrogen chloride in methanol (2 mL)
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-66f4df366fd545a7b75bdd3fa929298d
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156827B2

Notizen zur Reaktion

Wird geladen…