Dimethylformamide → 1-[6-(4-Fluorophenoxy)hexyl]-4-methyl-3-(4-pyridyl)-2-imidazolidinone

HRID 49270Notes

Reaction equation

HRID 49270 reaction equation
[CH3:1][CH:2]1[N:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[C:5](=NC#N)[NH:4][CH2:3]1.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1.CN(C=[O:37])C>>[F:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N:4]2[CH2:3][CH:2]([CH3:1])[N:6]([C:7]3[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=3)[C:5]2=[O:37])=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 15096974HCID 15096974, compoundHCID 178430630HCID 178430630, compound

Product 1

HCID 101725441-[6-(4-Fluorophenoxy)hexyl]-4-methyl-3-(4-pyridyl)-2-imidazolidinone

Procedure

To a solution of [5-methyl-1-(4-pyridyl)tetrahydro-1H-2-imidazolyliden]amino methanenitrile (60 mg, 0.30 mmol) in DMF (5 mL) at 0° C. was added sodium hydride (19 mg, 0.60 mmol, 75% in mineral oil) in one portion. The mixture was stirred at room temperature for 20 min followed by addition of 1-[(6-bromohexyl)oxy]-4-fluorobenzene (123 mg, 0.45 mmol) dissolved in DMF (3 ml) drop by drop. The resulting mixture was heated to 80° C. and stirred overnight (16 hours). The solvent was removed under reduced pressure and the crude residue was purified by column chromatography eluting with 15% methanol in ethyl acetate to afford the product (i.e., Compound 13) as a white solid (44 mg, 37%).

Workup

  1. temperatureThe resulting mixture was heated to 80° C.
  2. stirringstirred overnight (16 hours)
  3. customThe solvent was removed under reduced pressure
  4. customthe crude residue was purified by column chromatography
  5. washeluting with 15% methanol in ethyl acetate

Sources & evidence

ORD record
ord-afcd083fb1724431bfd4d8a4c112f510
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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