Potassium Iodide → HCID 25119537, compound

HRID 1182776Notes

Reaction equation

HRID 1182776 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]([CH2:25][O:26][C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[CH3:34])=[C:23]3[C:18]([NH:19][C:20]([CH3:38])([CH3:37])[C:21](=[O:36])[N:22]3[CH3:35])=[CH:17][CH:16]=2)=[C:11]([O:39][CH3:40])[CH:10]=1)(=[O:7])=[O:6].[CH2:41]([NH2:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[I-].[K+].C(OCC)(=O)C>CN(C)C=O>[CH2:41]([NH:48][CH2:2][CH2:3][CH2:4][S:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]([CH2:25][O:26][C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[CH3:34])=[C:23]3[C:18]([NH:19][C:20]([CH3:38])([CH3:37])[C:21](=[O:36])[N:22]3[CH3:35])=[CH:17][CH:16]=2)=[C:11]([O:39][CH3:40])[CH:10]=1)(=[O:7])=[O:6])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 58337192HCID 58337192, compound

Product 1

HCID 25119537HCID 25119537, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-[4-(3-chloropropylsulfonyloxy)-2-methoxyphenyl]-8-(5-fluoro-2-methylphenoxymethyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 1-40, 50.0 mg, 0.0846 mmol), benzylamine (92.4 μL, 0.846 mmol), and potassium iodide (16.9 mg, 0.102 mmol) was suspended in anhydrous N,N-dimethylformamide (0.4 mL) and stirred at 50° C. for 5 hours. After cooling down, ethyl acetate (50 mL) was added thereto. The organic layer was washed with water (50 mL) and saturated brine (30 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (21.4 mg) as a colorless amorphous product. (Yield 38%)

Workup

  1. temperatureAfter cooling down
  2. washThe organic layer was washed with water (50 mL) and saturated brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0bf4adff77bd4514aa8fbd9bb970672f
Source dataset
uspto-grants-2014_03
Patent number
US08664221B2

Reaction notes

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