Piperidine → 3-[4-(2-chlorophenyl)-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]propionic acid piperidide

HRID 2108062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2108062
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH2:19][C:20]([OH:22])=O)[S:17][C:13]=2[N:12]2[C:23]([CH3:26])=[N:24][N:25]=[C:11]2[CH:10]([CH3:27])[N:9]=1.O[N:29]1[C:33]2C=[CH:35][CH:36]=[CH:37][C:32]=2N=N1.N1CCCCC1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH2:19][C:20]([N:29]3[CH2:35][CH2:36][CH2:37][CH2:32][CH2:33]3)=[O:22])[S:17][C:13]=2[N:12]2[C:23]([CH3:26])=[N:24][N:25]=[C:11]2[CH:10]([CH3:27])[N:9]=1

Komponenten

6

Edukt 4

HCID 8082PiperidineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14699764HCID 14699764, Verbindung

Produkt 1

HCID 151069613-[4-(2-chlorophenyl)-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]propionic acid piperidideAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1.1 g of 3-[4-(2-chlorophenyl)-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]propionic acid in 15 ml of dimethylformamide are added 0.4 g of N-hydroxybenzotriazole and 0.25 g of piperidine and stirred at room temperature for 10 minutes. To the mixture is added 0.65 g of dicyclohexyl carbodiimide under ice-cooling and stirred for 1 hour and furthermore stirred at room temperature for 20 hours. The resulting dicyclohexylurea is filtered off and to the filtrate is added 50 ml of chloroform. The solution is washed with 5% aqueous sodium hydrogencarbonate solution and water and dried over anhydrous magnesium sulfate. After separating by filtration, the filtrate is concentrated under reduced pressure and the residue is crystallized from ethyl acetate. The precipitated crystals are collected by filtration and recrystallized from ethyl acetate to give 0.9 g of 3-[4-(2-chlorophenyl)-6,9-dimethyl-6H-thieno[3,2-f][1,2,4 ]triazolo[4,3-a][1,4]diazepin-2-yl]propionic acid piperidide as colorless crystals, melting at 157°-160° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringstirred for 1 hour
  3. stirringfurthermore stirred at room temperature for 20 hours
  4. filtrationThe resulting dicyclohexylurea is filtered off and to the filtrate
  5. additionis added 50 ml of chloroform
  6. washThe solution is washed with 5% aqueous sodium hydrogencarbonate solution and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter separating by filtration
  9. concentrationthe filtrate is concentrated under reduced pressure
  10. customthe residue is crystallized from ethyl acetate
  11. filtrationThe precipitated crystals are collected by filtration
  12. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ed4069dd01d84d9687997261abebeffd
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04937240

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