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

HRID 538873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538873
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]([NH2:32])=[CH:28][CH:27]=1.Cl>ClCCCl.CCCCO>[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([NH: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

6

Edukt 3

HCID 313Hydrochloric AcidHCID 12082Methyl 4-aminobenzoateHCID 547620851-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethylbutan-2-amine

Produkt 1

HCID 54760075methyl-4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)amino)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A solution of 1-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethyl-butan-2-amine (30 mg, 0.079 mmol), methyl-4-aminobenzoate (24 mg, 0.16 mmol) in 300 μL DCE and 300 μL n-BuOH was treated with 4N HCl (40 μL, 0.16 mmol) and refluxed overnight. The mixture was then partitioned between DCM and saturated NaHCO3 and the aqueous phase was extracted with DCM. The combined organic extracts were dried over Na2SO4, decanted and concentrated in vacuo. The residue was purified by PTLC using two 1 mm silica plates eluting with 5% MeOH (2N NH3)/DCM to provide methyl-4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)amino)benzoate. MS (ESI+) nil 450.19 [M+H]+.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. customThe mixture was then partitioned between DCM and saturated NaHCO3
  3. extractionthe aqueous phase was extracted with DCM
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by PTLC
  8. washeluting with 5% MeOH (2N NH3)/DCM

Quellen und Nachweise

ORD-Eintrag
ord-4235d003bca748829e9d3bc70d8700f8
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865752B2

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