Water → 4-[8-chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclopentyl-2-pyridinamine

HRID 456698Notes

Reaction equation

HRID 456698 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](F)[CH:19]=3)=[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.[CH:32]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33]1>>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:37][CH:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)[CH:19]=3)=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 2906CyclopentylamineHCID 8857Ethyl AcetateHCID 102689138-Chloro-2-(4-fluorophenyl)-3-(2-fluoro-4-pyridinyl)imidazo[1,2-a]pyridine

Product 1

HCID 101795364-[8-chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclopentyl-2-pyridinamineYield 76%

Conditions

Temperature
150 °C

Procedure

8-Chloro-2-(4-fluorophenyl)-3-(2-fluoro-4-pyridinyl)imidazo[1,2-α]pyridine (0.10 g, 0.29 mmol) was dissolved in cyclopentylamine (5 mL). This solution was heated in a glass tube at 150° C. for 72 hours. Ethyl acetate and water were added to the reaction mixture and the phases were separated. The organic phase was washed with water, dried (magnesium sulfate), filtered and concentrated to a solid. This solid was purified by silica gel chromatography (1:1 ethyl acetate:hexane) to give 4-[8-chloro-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-3-yl]-N-cyclopentyl-2-pyridinamine (90 mg, 76%) as a white foam. 1H NMR (CDCl3): δ 8.26 (d, 1H), 8.06 (d, 1H), 7.73 (q, 2H), 7.34 (d, 1H), 7.05 (t, 2H), 6.77 (t, 1H), 6.65 (dd, 1H), 6.4 (s, 1H), 4.85 (d, 1H), 3.92 (m, 1H), 2.0–1.4 (m, 8H); 19F NMR (CDCl3) δ −114.07; MS m/z 407 (M+1).

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with water
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated to a solid
  6. customThis solid was purified by silica gel chromatography (1:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-eb95d8ccf10040c7a25d9a3859a9b014
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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