Diisopropylethylamine → N-(4-(4,5,6,7-tetrahydrobenzothiazol-6-ylamino)butyl)benzothiazole-2-carboxamide

HRID 1942383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942383
O[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1)=[O:8].[S:18]1[C:22]2[CH2:23][CH:24]([NH2:27])[CH2:25][CH2:26][C:21]=2[N:20]=[CH:19]1.CCN(C(C)C)C(C)C.[I-].C(C[P+](C)(C)C)#N.C([O-])(O)=O.[Na+]>C(#N)CC.C(Cl)Cl>[S:18]1[C:22]2[CH2:23][CH:24]([NH:27][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]3[S:10][C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)=[O:8])[CH2:25][CH2:26][C:21]=2[N:20]=[CH:19]1

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 451219024,5,6,7-Tetrahydrobenzo[d]thiazol-6-amineHCID 66937473N-(4-hydroxybutyl)benzothiazole-2-carboxamide

Produkt 1

HCID 66937369N-(4-(4,5,6,7-tetrahydrobenzothiazol-6-ylamino)butyl)benzothiazole-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 7854PropionitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 339 mg (1.4 mmol) N-(4-hydroxybutyl)benzothiazole-2-carboxamide, 198 mg (1.2 mmol) 4,5,6,7-tetrahydro-benzothiazol-6-yl-amine and 210 mg (1.6 mmol) DIPEA in 6 mL of propionitrile is added 0.39 g (1.6 mmol) cyanomethyltrimethylphosphonium iodide under argon. The mixture is heated for 2 hours at 90° C. After cooling down to room temperature 10 mL of saturated NaHCO3 solution and 20 mL of CH2Cl2 are added. The organic phase is extracted with 10 mL of water three times. After drying and removing of the solvent in vacuum the brown oil received is purified via silica gel chromatography.

Aufarbeitung

  1. additionare added
  2. extractionThe organic phase is extracted with 10 mL of water three times
  3. customAfter drying
  4. customremoving of the solvent in vacuum the brown oil
  5. customreceived is purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d42f12f0e1f4473689863671b910d587
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389555B2

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