1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[3-Amino-2-hydroxy-3-oxo-1-(phenylmethyl)propyl]-2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxamide

HRID 2280957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280957
C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.[C:22]1([C:28]2[N:29]=[CH:30][N:31]([C:33]3[C:38]([C:39]([OH:41])=O)=[CH:37][CH:36]=[CH:35][N:34]=3)[CH:32]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.[NH2:43][CH:44]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH:45]([OH:49])[C:46]([NH2:48])=[O:47].C([O-])(O)=O.[Na+]>ClCCl.CCN(CC)CC>[NH2:48][C:46](=[O:47])[CH:45]([OH:49])[CH:44]([NH:43][C:39]([C:38]1[C:33]([N:31]2[CH:32]=[C:28]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:29]=[CH:30]2)=[N:34][CH:35]=[CH:36][CH:37]=1)=[O:41])[CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516892Sodium BicarbonateHCID 225938833-Amino-2-hydroxy-4-phenylbutanamide hydrochlorideHCID 667200892-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 66720082N-[3-Amino-2-hydroxy-3-oxo-1-(phenylmethyl)propyl]-2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxamideAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel3×

Reaktionsbedingungen

Temperatur
2 °C

Versuchsvorschrift

0.75 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), 0.51 g of hydroxyl-benzotriazole (HOBt) and 0.55 ml of triethylamine (Et3N) were successively added to a solution of 1.0 g of 2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylic acid (3.77 mmol) in 50 ml of dichloromethane at 0-4° C., and the mixture was stirred at 0-4° C. for 1 hour. 0.9 g of 3-amino-2-hydroxy-4-phenylbutanamide hydrochloride (3.9 mmol) and 0.55 ml of Et3N were then added and, after about 5 minutes, a pH of 8-9 was adjusted by adding 0.5 ml of Et3N. The mixture was stirred at 0-4° C. for 1 hour and then at room temperature overnight. 50 ml of saturated NaHCO3 solution were then added to the mixture, and the organic phase was separated off. Drying and evaporating the solvent resulted in 620 mg of a reddish oil, which was reacted further immediately without further purification.

Aufarbeitung

  1. stirringThe mixture was stirred at 0-4° C. for 1 hour
  2. customat room temperature
  3. customovernight
  4. customthe organic phase was separated off
  5. customDrying
  6. customevaporating the solvent

Quellen und Nachweise

ORD-Eintrag
ord-45529239508942b5b924aa8016ecd91c
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139557B2

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