Methyl iodide → HCID 57671929, compound

HRID 1038501Notes

Reaction equation

HRID 1038501 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-9ca30bce2558411a8483a9ac3fe74d02
Source dataset
uspto-grants-2013_10
Patent number
US08551991B2

Reaction notes

Loading…