Methyl iodide → HCID 25184907, compound

HRID 1878086Notes

Reaction equation

HRID 1878086 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([OH:14])[CH:11]=[C:10]([C:15]([F:18])([F:17])[F:16])[N:9]=2)=[N:6][CH:7]=1.[C:19]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:19][O:14][C:12]1[CH:11]=[C:10]([C:15]([F:18])([F:17])[F:16])[N:9]=[C:8]([C:5]2[N:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178507455HCID 178507455, compound

Product 1

HCID 25184907HCID 25184907, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of compound of example 15 (0.100 g, 0.390 mmol) in DMF (3 mL), was added K2CO3 (0.080 g, 0.58 mmol) and stirred at 25° C. for 10 minutes. To the reaction mixture methyl iodide (0.083 g, 0.58 mmol) was added slowly and stirred at 25° C. for 1 hour. DMF was removed under vacuum and reaction mass quenched with water, extracted with ethyl acetate (3×10 mL), dried over sodium sulfate and concentrated to obtain the crude product, which was purified by column chromatography using silica gel and 8% methanol in chloroform as an eluent to obtain the title compound.

Workup

  1. stirringstirred at 25° C. for 1 hour
  2. customDMF was removed under vacuum and reaction mass
  3. customquenched with water
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto obtain the crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b24b55618d1b4f389af53e82d556d46b
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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