Methyl iodide → HCID 57671929, compound

HRID 871997Notes

Reaction equation

HRID 871997 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:41])=[C:6]([CH:40]=1)[O:7][CH2:8][C:9]1[C:10]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)=[O:31])=[CH:25][C:24]=2[O:38][CH3:39])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]([CH3:19])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[NH:14]2.[C:42](=O)([O-])[O-].CI>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:41])=[C:6]([CH:40]=1)[O:7][CH2:8][C:9]1[C:10]([C:23]2[CH:28]=[CH:27][C:26]([N:29]([CH3:42])[C:30]([C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)=[O:31])=[CH:25][C:24]=2[O:38][CH3:39])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]([CH3:19])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[NH:14]2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 19660Carbonate IonHCID 57671733HCID 57671733, compound

Product 1

HCID 57671929HCID 57671929, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-(5-fluoro-2-methylphenoxymethyl)-7-[2-methoxy-4-(pyridin-4-ylcarbonylamino)phenyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 14-21, 13.9 mg, 0.0251 mmol), cessium carbonate (41.7 mg, 0.128 mmol), and methyl iodide (4.7 μL, 0.075 mmol) was suspended in anhydrous N,N-dimethylformamide (0.5 ml) and stirred for 3 hours at room temperature. The mixture was diluted with ethyl acetate (10 mL). The mixture was washed with water (10 mL) and saturated brine (10 mL) successively, 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 (4.6 mg) as a yellow amorphous product. (Yield 32%)

Workup

  1. washThe mixture was washed with water (10 mL) and saturated brine (10 mL) successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e6c1d6d2a67f4a8cb67930ab7f611b94
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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