Formaldehyde → N-(3',6'-dihydro-2,4'-bipyridin-1'(2'H)-ylmethyl)-3,5-dimethoxybenzamide

HRID 490178

Reaktionsgleichung

Reaktionsgleichung von HRID 490178
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=1.C=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1)[C:21]([NH2:23])=[O:22].[C:29](=O)([O-])[O-].[K+].[K+]>C(O)C>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:9][CH2:10][N:11]([CH2:29][NH:23][C:21](=[O:22])[C:20]2[CH:24]=[C:25]([O:27][CH3:28])[CH:26]=[C:18]([O:17][CH3:16])[CH:19]=2)[CH2:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 728783,5-DimethoxybenzamideHCID 688728301',2',3',6'-Tetrahydro-2,4'-bipyridine hydrochloride

Produkt 1

HCID 68875562N-(3',6'-dihydro-2,4'-bipyridin-1'(2'H)-ylmethyl)-3,5-dimethoxybenzamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl hydrochloride (20 mg, 0.10 mmol, Saari, W. S.; et al. J. Med. Chem. 1984, 27, 1182), paraformaldehyde (30 mg, 1 mmol), 3,5-dimethoxybenzamide (91 mg, 0.5 mmol, Aldrich), and 42 mg of potassium carbonate (0.3 mmol) in 2.5 mL absolute ethyl alcohol was heated to reflux under nitrogen overnight. The mixture was cooled to room temperature, filtered, and the solvent was removed. The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate) to give 19 mg (55%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ 2.59 (m, 2H), 2.79 (t, J=4 Hz, 2H), 3.30 (m, 2H), 3.79 (s, 3H), 3.80 (s, 3H), 4.25 (d, J=5 Hz, 2H), 6.65 (s, 1H), 6.71 (m, 1H), 7.02 (s, 2H), 7.22 (m, 1H), 7.52 (d, J=6 Hz, 1H), 7.75 (t, J=6 Hz), 8.52 (m, 1H), 8.88 (t, J=5 Hz, 1H); MS (ESI/APCI−) m/e 352 (M−H)+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen overnight
  3. filtrationfiltered
  4. customthe solvent was removed
  5. customThe residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-31b710855b084b50abdaa1a302ee154e
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528134B2

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