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

HRID 981057

Reaction equation

HRID 981057 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
75 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8d777e38b5e84e1ba4e32a92fdea0dc4
Source dataset
uspto-grants-1991_02
Patent number
US04990518

Linked notes

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