Pyridine → HCID 25196652, compound

HRID 1971621Notes

Reaction equation

HRID 1971621 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 l, 0.075 g, 0.00033 mol) was dissolved in tetrahydrofuran (5.0 mL) and pyridine (29 uL, 0.00036 mol) was added. Rxn 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-578b6dc5a47140e5987b95c64281f387
Source dataset
uspto-grants-2013_04
Patent number
US08431608B2

Reaction notes

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