Triethylamine → Pyridine-3,4-dicarboxylic acid bis-[(4-phenyl-butyl)-amide]

HRID 1454128

Reaktionsgleichung

Reaktionsgleichung von HRID 1454128
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[C:3]([C:10]([OH:12])=O)[CH:2]=1.O.ON1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([N:37]([CH2:40][CH3:41])CC)C.Cl.CN(C)[CH2:45][CH2:46]CN=C=NCC>CN(C=O)C>[C:18]1([CH2:45][CH2:46][CH2:41][CH2:40][NH:37][C:10]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][C:4]=2[C:7]([NH:34][CH2:33][CH2:32][CH2:31][CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:9])=[O:12])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 10273Cinchomeronic acidHCID 83242BenzenebutanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 18727498Pyridine-3,4-dicarboxylic acid bis-[(4-phenyl-butyl)-amide]Ausbeute 102,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3,4-Pyridinedicarboxylic acid (1 g; 6.0 mmol) is slurried in DMF (50 mL) at ambient temperature. To this reaction mixture is added sequentially 1-hydroxybenzotriazole hydrate (2.43 g; 18.0 mmol), 4-phenylbutylamine (2.08 mL; 13.2 mmol), triethylamine (1.67 mL; 12.0 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.87 g; 15.0 mmol). The reaction mixture is stirred for 18 hours at ambient temperature. The batch is poured onto ethyl acetate (300 mL), then extracted sequentially with water (100 mL), 1N HCl (100 mL), saturated aqueous sodium bicarbonate (50 mL), and brine (50 mL). The organic phase is dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (2.65 g) as a semi-solid. ESMS: MH+ 430.0.

Aufarbeitung

  1. additionThe batch is poured onto ethyl acetate (300 mL)
  2. extractionextracted sequentially with water (100 mL), 1N HCl (100 mL), saturated aqueous sodium bicarbonate (50 mL), and brine (50 mL)
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-444ef3a4d4a34159ba514961f4fdf438
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476680B2

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