Dimethylformamide → HCID 9904333, Verbindung

HRID 636533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636533
[NH:1]1[CH:6]=[C:5]([C:7]([OH:9])=O)[C:4](=[O:10])[C:3]2[CH2:11][CH2:12][CH2:13][C:2]1=2.CN(C=O)C.ClC(OCC)=O.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1>C1COCC1.O>[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH:32][C:7]([C:5]2[C:4](=[O:10])[C:3]3[CH2:11][CH2:12][CH2:13][C:2]=3[NH:1][CH:6]=2)=[O:9])=[CH:29][CH:28]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10928Ethyl chloroformateHCID 754524-MethoxybenzylamineHCID 122914536,7-Dihydro-4-hydroxy-5H-cyclopenta[b]pyridine-3-carboxylic acid

Produkt 1

HCID 9904333HCID 9904333, VerbindungAusbeute 48,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A quantity of 100 mg (0.61 mmole, 1.0 eq) of 4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridin-4-one-3-carboxylic acid is dissolved in 5 mL THF and 1 mL DMF and treated at 0° C. with 0.18 mL (1.2 mmole, 2.2 eq) TEA followed by 0.12 mL (1.2 mmole, 2.2 eq) of ethyl chloroformate. The resulting solution is stirred for 30 min. at which time 0.17 mL (1.2 mmole, 2.2 eq) of 4-methoxybenzylamine is added. The solution is allowed to warm to room temperature for 1 hr before the addition of 20 mL of H2O, the THF is removed under reduced pressure, and the resulting solid is filtered and washed with H2O and then Et2O. The resulting solid is slurried in 1 mL EtOH and 5 mL 10% NaOH, warmed to 90° C. for 10 min., cooled to 0° C., and pH adjusted to 9.0 with 3N HCl. The resulting solid is filtered, washed with H2O, Et2O, and purified by chromatography (silica gel, 10% CH3OH/CH2Cl2), to yield 89 mg of N-(4-Methoxybenzyl)-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridin-4-one-3-carboxamide (compound 1), mp 240-241° C.

Aufarbeitung

  1. additionis added
  2. customthe THF is removed under reduced pressure
  3. filtrationthe resulting solid is filtered
  4. washwashed with H2O
  5. temperaturecooled to 0° C.
  6. filtrationThe resulting solid is filtered
  7. washwashed with H2O, Et2O
  8. custompurified by chromatography (silica gel, 10% CH3OH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-d159151306ba4f0abbf0a44ddfdcd251
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194427B1

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