Pyridine → HCID 25196652, compound

HRID 556318Notes

Reaction equation

HRID 556318 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:9]([NH2:11])[N:10]=2)[CH:7]=1.N1C=CC=CC=1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](Cl)=[O:33])=[CH:27][CH:26]=1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:9]([NH:11][C:32](=[O:33])[CH2:31][C:28]3[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 37449884-Fluorophenylacetyl chlorideHCID 57607467HCID 57607467, compound2×

Product 1

HCID 25196652HCID 25196652, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

6-fluoro-3-phenylimidazo[1,2-a]pyridin-2-amine (compound 1, 0.075 g, 0.00033 mol) was dissolved in tetrahydrofuran (5.0 mL) and pyridine (29 uL, 0.00036 mol) was added. R×n cooled to 0° C. and 4-fluorophenylacetyl chloride (48 uL, 0.00036 mol) was added. The reaction was stirred at 0° C. for 30 minutes. The solvent was removed and the crude product was partioned between water (25 mL) and EtOAc (25 mL). The layers were separated and the organic layer was washed 3×20 mL with water. The organic layer was dried (magnesium sulfate) then chromatographed on silica (70% ethyl acetate/hexanes) to give N-(6-fluoro-3-phenylimidazo[1,2-a]pyridin-2-yl)-2-(4-fluorophenyl)acetamide Rf 0.37, 70% ethyl acetate/hexanes; MS m/z 364 (M+H). SH-SY5Y_EC50 (μM): 0.7321.

Workup

  1. customThe solvent was removed
  2. customThe layers were separated
  3. washthe organic layer was washed 3×20 mL with water
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. customthen chromatographed on silica (70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3b118b8c91394824a6f7d0aae1cc70d9
Source dataset
uspto-grants-2011_11
Patent number
US08058274B2

Reaction notes

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