2-(Dimethylamino)ethanol → N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-N-(2-dimethylaminoethyl)-5-isoquinolinesulfonamide

HRID 1090590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090590
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH:6]=[CH:7][CH2:8][N:9]([CH2:11][CH2:12][NH:13][S:14]([C:17]2[C:18]3[CH:19]=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH3:10])=[CH:4][CH:3]=1.[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][CH2:8][N:9]([CH2:11][CH2:12][N:13]([CH2:32][CH2:31][N:30]([CH3:34])[CH3:29])[S:14]([C:17]2[C:18]3[CH:19]=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:15])=[O:16])[CH3:10])=[CH:27][CH:28]=1

Komponenten

7

Edukt 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53675817N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-5-isoquinolinesulfonamide

Produkt 1

HCID 53740000N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-N-(2-dimethylaminoethyl)-5-isoquinolinesulfonamideAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1.0 g of the amorphous compound obtained in Example 190, 0.267 g of 2-dimethylamino ethanol and 0.982 g of triphenylphosphine in 5 ml of tetrahydrofuran, was added dropwise a solution of 0.652 g of diethyl azodicarboxylate in 2 ml of tetrahydrofuran with stirring under ice cooling. After 2 hours, the reaction mixture was concentrated under a reduced pressure to remove tetrahydrofuran, and resulting residue was dissolved in 10 ml of ethyl acetate and extracted three times with 10 ml of 1N hydrochloric acid. The aqueous layer was alkalized with sodium bicarbonate and extracted three times with 10 ml of ethyl acetate, and the organic layer was dried over magnesium sulfate and evaporated to removed the solvent under a reduced pressure. The resulting residue was then applied to a silica gel column and eluted with 3% methanol in chloroform, to obtain 0.77 g of the title compound as a colorless oil.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under a reduced pressure
  2. customto remove tetrahydrofuran
  3. customresulting residue
  4. extractionextracted three times with 10 ml of 1N hydrochloric acid
  5. extractionextracted three times with 10 ml of ethyl acetate
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. customevaporated
  8. customto removed the solvent under a reduced pressure
  9. washeluted with 3% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-846769da0c254cc8900d8edbc13e9ef4
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081246

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