Diisopropylethylamine → HCID 178462095, Verbindung

HRID 1629814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629814
[N:1]1([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].CCN(C(C)C)C(C)C.Cl.[Cl:27][C:28]1[CH:39]=[CH:38][C:31]2[NH:32][C:33]([C@@H:35]([NH2:37])[CH3:36])=[N:34][C:30]=2[CH:29]=1>CN(C=O)C>[Cl:27][C:28]1[CH:39]=[CH:38][C:31]2[NH:32][C:33]([C@@H:35]([NH:37][C:12](=[O:14])[C:11]3[CH:10]=[CH:9][C:8]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][C:2]4=[O:7])=[CH:16][CH:15]=3)[CH3:36])=[N:34][C:30]=2[CH:29]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 230877894-(3-Oxomorpholino)benzoic acidHCID 178461860(1S)-1-(5-chloro-1h-benzimidazol-2-yl)-ethylamine-hydrochloride

Produkt 1

HCID 178462095HCID 178462095, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

254 mg (1.15 mmol) 4-(morpholin-3-on-4-yl)-benzoic acid (prepared by synthesis sequence analogously to Example 30a, 2d and 21a) are placed in 5 ml DMF and 428 mg (1.0 mmol) PfTU and 514 μl (3.0 mmol) DIPEA are added. After stirring at ambient temperature for 10 minutes 232 mg (1.0 mmol) (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamine-hydrochloride are added and the mixture is stirred for 16 hours at ambient temperature. Then the reaction mixture is filtered through basic aluminium oxide and evaporated down i. vac. The residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/methanol 100:0->90:10), the corresponding fractions are evaporated down i. vac., the residue is dissolved in acetonitrile/water and lyophilised.

Aufarbeitung

  1. additionare added
  2. filtrationThen the reaction mixture is filtered through basic aluminium oxide
  3. customevaporated down i
  4. customThe residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/methanol 100:0->90:10)
  5. customthe corresponding fractions are evaporated down i
  6. dissolution, the residue is dissolved in acetonitrile/water

Quellen und Nachweise

ORD-Eintrag
ord-d6df6130b1674021b00577bfff91d254
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791103B2

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