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p-Toluenesulfonic acid monohydrate → N-[2-(diethylamino)ethyl]-N-(2-{[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]amino}ethyl)-3-[2-(1-naphthyl)ethoxy]propanamide ditosylate

HRID 556722
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Reaktionsgleichung

Reaktionsgleichung von HRID 556722
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:13]([N:15]([CH2:52][CH3:53])[CH2:16][CH2:17][N:18]([CH2:36][CH2:37][NH:38][CH2:39][CH2:40][C:41]1[C:49]2[S:48][C:47](=[O:50])[NH:46][C:45]=2[C:44]([OH:51])=[CH:43][CH:42]=1)[C:19](=[O:35])[CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)[CH3:14]>CO>[S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:12])=[CH:3][CH:4]=1)([OH:11])(=[O:10])=[O:9].[S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:12])=[CH:3][CH:4]=1)([OH:11])(=[O:10])=[O:9].[CH2:52]([N:15]([CH2:13][CH3:14])[CH2:16][CH2:17][N:18]([CH2:36][CH2:37][NH:38][CH2:39][CH2:40][C:41]1[C:49]2[S:48][C:47](=[O:50])[NH:46][C:45]=2[C:44]([OH:51])=[CH:43][CH:42]=1)[C:19](=[O:35])[CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)[CH3:53]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 16035068Azd-3199

Produkt 1

HCID 86623637N-[2-(diethylamino)ethyl]-N-(2-{[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]amino}ethyl)-3-[2-(1-naphthyl)ethoxy]propanamide ditosylateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

p-Toluenesulfonic acid monohydrate (667.33 mg) was added in one portion to a solution of N-[2-(diethylamino)ethyl]-N-(2-{[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]amino}ethyl)-3-[2-(1-naphthyl)ethoxy]propanamide (1 g) in methanol (10 mL) producing a clear solution. This was stirred at room temperature for 30 mins then the solvent was removed in vacuo. The residue was stirred in diethyl ether (20 mL) at room temperature for 16 h then the solvent was removed and methyl t-butyl ether (20 mL) was added. This mixture was then stirred at room temperature for 16 h before the resulting solid was collected by filtration and washed with methyl t-butyl ether (5 mL). The title compound was dried in vacuo at room temperature for 16 h to leave the title compound as an amorphous solid (1.18 g).

Aufarbeitung

  1. customproducing a clear solution
  2. customthe solvent was removed in vacuo
  3. stirringThe residue was stirred in diethyl ether (20 mL) at room temperature for 16 h
  4. customthe solvent was removed
  5. additionmethyl t-butyl ether (20 mL) was added
  6. stirringThis mixture was then stirred at room temperature for 16 h before the resulting solid
  7. filtrationwas collected by filtration
  8. washwashed with methyl t-butyl ether (5 mL)
  9. dry with materialThe title compound was dried in vacuo at room temperature for 16 h

Quellen und Nachweise

ORD-Eintrag
ord-5887adbbf8cf4be496ba830a05b30ac4
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08058294B2

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