Methyl iodide → HCID 59292894, compound

HRID 2391866Notes

Reaction equation

HRID 2391866 reaction equation
CI.[CH3:3][C:4]1([CH3:42])[NH:9][CH2:8][CH2:7][N:6]([CH2:10][C:11]2[N:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[C:21]4[N:22]=[CH:23][CH:24]=[N:25][C:26]=4[C:27]([C:30]4[C:35]([Cl:36])=[C:34]([O:37][CH3:38])[CH:33]=[C:32]([O:39][CH3:40])[C:31]=4[Cl:41])=[CH:28][CH:29]=3)=[O:19])=[CH:13][CH:12]=2)[CH2:5]1.[C:43](=O)([O-])[O-].[K+].[K+]>CC#N>[CH3:3][C:4]1([CH3:42])[N:9]([CH3:43])[CH2:8][CH2:7][N:6]([CH2:10][C:11]2[N:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[C:21]4[N:22]=[CH:23][CH:24]=[N:25][C:26]=4[C:27]([C:30]4[C:31]([Cl:41])=[C:32]([O:39][CH3:40])[CH:33]=[C:34]([O:37][CH3:38])[C:35]=4[Cl:36])=[CH:28][CH:29]=3)=[O:19])=[CH:13][CH:12]=2)[CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59292881HCID 59292881, compound

Product 1

HCID 59292894HCID 59292894, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl iodide (15 μL, 0.24 mmol, 1.2 equiv) was added to a mixture of 8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [6-(3,3-dimethyl-piperazin-1-ylmethyl)-pyridin-3-yl]-amide (Example 112) (115 mg, 0.2 mmol) and potassium carbonate (33 mg, 0.24 mmol, 1.2 equiv) in CH3CN (4 mL). The reaction mixture was stirred for 72 h at rt, quenched by addition of a saturated aqueous solution of NaHCO3 and extracted with EtOAc. The organic layer was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/NH3aq, 99:1→DCM/MeOH/NH3aq, 96:3:1) followed by trituration id Et2O to afford 27 mg of the title compound as a yellow solid. Title compound: ESI-MS: 595.1/596.6 [M+H]+; tR=3.54 min (System 1); TLC: Rf=0.17 (DCM/MeOH, 9:1).

Workup

  1. customquenched by addition of a saturated aqueous solution of NaHCO3
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with a saturated aqueous solution of NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (DCM/NH3aq, 99:1→DCM/MeOH/NH3aq, 96:3:1)

Sources & evidence

ORD record
ord-79e47ee36c554f248146fafadb01e8b1
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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