Methylparaben → methyl-4-((6-(2-(dimethylamino)-1-(1H-imidazol-yl)butyl)benzo[d]thiazol-2-yl)oxy)benzoate

HRID 538879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538879
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]([N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)[CH:12]([N:15]([CH3:17])[CH3:16])[CH2:13][CH3:14])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([O:32][C:2]2[S:3][C:4]3[CH:10]=[C:9]([CH:11]([N:18]4[CH:22]=[CH:21][N:20]=[CH:19]4)[CH:12]([N:15]([CH3:17])[CH3:16])[CH2:13][CH3:14])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 547620851-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethylbutan-2-amine

Produkt 1

HCID 54760635methyl-4-((6-(2-(dimethylamino)-1-(1H-imidazol-yl)butyl)benzo[d]thiazol-2-yl)oxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 1-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethyl-butan-2-amine (54 mg, 0.14 mmol), methyl-4-hydroxybenzoate (21.7 mg, 0.14 mmol) and potassium carbonate (21.6 mg, 0.16 mmol) in 1 mL of DMF was heated at 80° C. overnight. The mixture was concentration in vacuo and the residue partitioned between water and DCM. After extracting the aqueous layer, the combined DCM extracts were dried over Na2SO4, decanted and concentrated in vacuo. The residue was purified using PTLC and eluting with 5% MeOH (2N NH3)/DCM to provide methyl-4-((6-(2-(dimethylamino)-1-(1H-imidazol-yl)butyl)benzo[d]thiazol-2-yl)oxy)benzoate. MS (ESI) m/z 451.17 [M+H]+.

Aufarbeitung

  1. concentrationconcentration in vacuo
  2. customthe residue partitioned between water and DCM
  3. extractionAfter extracting the aqueous layer
  4. dry with materialthe combined DCM extracts were dried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washeluting with 5% MeOH (2N NH3)/DCM

Quellen und Nachweise

ORD-Eintrag
ord-74c7b47d3f584af98238e4d1315e337b
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865752B2

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