Potassium Carbonate → N-(2-(2-aminoethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide

HRID 870214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870214
Cl.Cl.[NH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][NH2:9].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:18]=[C:19]2[C:24](=[C:25]([Cl:27])[CH:26]=1)[CH2:23][N:22]([CH3:28])[CH2:21][CH:20]2[C:29]1[CH:30]=[C:31]([S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>CN(C=O)C.O>[NH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][NH:9][S:35]([C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([CH:20]2[C:19]3[C:24](=[C:25]([Cl:27])[CH:26]=[C:17]([Cl:16])[CH:18]=3)[CH2:23][N:22]([CH3:28])[CH2:21]2)[CH:30]=1)(=[O:37])=[O:36]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 28290232,2'-Oxybis(ethylamine) hydrochlorideHCID 866723303-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride2×

Produkt 1

HCID 67460236N-(2-(2-aminoethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol, 5.52 equiv) in DMF (20 mL), potassium carbonate (2.0 g, 14.39 mmol, 14.05 equiv) and 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride (intermediate 1.6) (400 mg, 1.02 mmol, 1.00 equiv). The resulting solution was stirred overnight at room temperature at which time it was diluted with 100 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic layers were combined and dried over sodium sulfate and concentrated under vacuum. This resulted in 60 mg (13%) of N-(2-(2-aminoethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide as a yellow solid.

Aufarbeitung

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. extractionThe resulting solution was extracted with 3×30 mL of ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 60 mg (13%) of N-(2-(2-aminoethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-6d8da7c6af704851ab9f34eb632068e4
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969377B2

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