Water → N'-[3-[(2E)-3-(dimethylamino)-2-propenoyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-yl]-N,N-dimethylimidoformamide

HRID 456686Notes

Reaction equation

HRID 456686 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C:18](=[O:20])[CH3:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(OCC)(=O)C.O.CO[CH:30](OC)[N:31]([CH3:33])[CH3:32]>>[CH3:30][N:31]([CH3:33])/[CH:32]=[CH:19]/[C:18]([C:8]1[N:4]2[CH:5]=[CH:6][CH:7]=[C:2]([N:1]=[CH:3][N:4]([CH3:8])[CH3:5])[C:3]2=[N:10][C:9]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:20]

Participants

5

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 695497661-[8-Amino-2-(4-fluorophenyl)imidazo[1,2-a)pyridin-3-yl]ethanone

Product 1

HCID 69548821N'-[3-[(2E)-3-(dimethylamino)-2-propenoyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-yl]-N,N-dimethylimidoformamideYield 62%

Procedure

A solution of 1-[8-amino-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-3-yl]ethanone (150 mg, 0.56 mmol) in N,N-dimethylformamide dimethyl acetal (5 mL) was heated at reflux for 6 days. The mixture was cooled to room temperature, ethyl acetate and water were added. The phases were separated and the organic layer was washed with brine. The aqueous layer was extracted with ethyl acetate and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by silica gel chromatography (1:1 acetone:ethyl acetate) gave 130 mg (62%) of N′-[3-[(2E)-3-(dimethylamino)-2-propenoyl]-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-8-yl]-N,N-dimethylimidoformamide as a foam. 1H NMR (CDCl3): δ 9.28 (d, 1H), 8.53 (s, 1H), 7.76 (q, 2H), 7.62 (d, 1H), 7.13 (t, 2H), 6.87 (m, 2H), 5.12 (d, 1H), 2.4–3.3 (m, 12H); MS m/z 380 (M+1).

Workup

  1. temperatureat reflux for 6 days
  2. customThe phases were separated
  3. washthe organic layer was washed with brine
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organics were dried over magnesium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-d9ea85e9a273484dba301e0ce3525d81
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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