Dimethylacetamide → N-cyclohexyl-5-[(5H-imidazo[4,5-c]pyridin-5-yl)methyl]N-methyl-2-furancarboxamide

HRID 981057

Reaktionsgleichung

Reaktionsgleichung von HRID 981057
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[N:3]=[CH:2]1.[CH2:10](Cl)[C:11]1[O:15]C=[CH:13][CH:12]=1.[CH3:17][C:18]([N:20]([CH3:22])[CH3:21])=[O:19]>>[CH:21]1([N:20]([CH3:22])[C:18]([C:17]2[O:15][C:11]([CH2:10][N:9]3[CH:8]=[CH:7][C:6]4=[N:3][CH:2]=[N:1][C:5]4=[CH:4]3)=[CH:12][CH:13]=2)=[O:19])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Komponenten

4

Edukt 3

HCID 31374DimethylacetamideHCID 67504Imidazo(4,5-b)pyridineHCID 2195202-(Chloromethyl)furan

Produkt 1

HCID 20071642N-cyclohexyl-5-[(5H-imidazo[4,5-c]pyridin-5-yl)methyl]N-methyl-2-furancarboxamideAusbeute 65 %

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a stirred solution of imidazopyridine (150 mg, 1.25 mmol) in dimethylacetamide (30 mL) under argon, furfuryl chloride (product of Example H) (320 mg. 1.25 mmol) was added in one portion. The reaction temperature was slowly raised to 75° C. and was stirred for 60 hr. The reaction flask was cooled to room temperature and the solvent was removed under reduced pressure at <45° C. The residue obtained was triturated with excess of dry ether and filtered. The crude product (410 mg) was chromatographed (silica gel, CH2Cl2 :MeOH:NH4OH::90:10:1) to give the title compound (265 mg, 65%) as white solid, mp 189-90° C., 1H NMR (CDCl3) 1H NMR (CDCl3) 0.85 -1.9(m, 13H), 3.6-3.8 & 4.3-4.45(m, 1H), 5.62 (s, 2H), 6.62 (brs, 1H), 6.82 (brs, 1H), 7.73 (dd, J=7 Hz, 1H), 7.85 (dd, J=3,7 Hz, 1H), 8.57 (s, 1H), 8.8 ppm (s, 1H), Anal calcd. for C19H22N4O2 0.5H2O: C, 65.70,H,6.62, N, 16.11. Found: C, 65.65, H, 6.71, N, 16.06.

Aufarbeitung

  1. temperatureThe reaction flask was cooled to room temperature
  2. customthe solvent was removed under reduced pressure at <45° C
  3. customThe residue obtained
  4. customwas triturated with excess of dry ether
  5. filtrationfiltered
  6. customThe crude product (410 mg) was chromatographed (silica gel, CH2Cl2 :MeOH:NH4OH::90:10:1)

Quellen und Nachweise

ORD-Eintrag
ord-8d777e38b5e84e1ba4e32a92fdea0dc4
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990518

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