Methyl iodide → HCID 68870406, compound

HRID 730001Notes

Reaction equation

HRID 730001 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:13][C:12]([C:14]2[N:19]=[C:18]3[N:20]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:21]([N:23]=[CH:24][N:25]([CH3:27])[CH3:26])=[N:22][C:17]3=[CH:16][CH:15]=2)=[C:11]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:10]=1.IC.[C:40]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[N:13]([CH3:40])[C:12]([C:14]2[N:19]=[C:18]3[N:20]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:21]([N:23]=[CH:24][N:25]([CH3:27])[CH3:26])=[N:22][C:17]3=[CH:16][CH:15]=2)=[C:11]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 68870022HCID 68870022, compound

Product 1

HCID 68870406HCID 68870406, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir N′-{5-[2-(2,6-dichlorophenyl)-5-phenyl-3H-imidazol-4-yl]-3-isobutyl-3H-imidazo[4,5-b]pyridin-2-yl}-N,N-dimethylformamidine prepared essentially as described in EXAMPLE 63 (0.10 g, 0.188 mmol), iodomethane (0.040 g, 0.282 mmol), and Cs2CO3 (0.09 g, 0.28 mmol) in DMF (1.5 mL) at RT for about 24 h. Extract with EtOAc and wash with water (3×), saturated aqueous NaCl, then dry over Na2SO4. Filter and concentrate to give a mixture of methyl isomers. Purify (silica gel chromatography) eluting with 1:1:0.4 CH2Cl2:acetonitrile:hexanes to give the title compound (0.02 g).

Workup

  1. customprepared essentially
  2. extractionExtract with EtOAc
  3. washwash with water (3×), saturated aqueous NaCl
  4. dry with materialdry over Na2SO4
  5. filtrationFilter
  6. concentrationconcentrate
  7. customto give
  8. additiona mixture of methyl isomers
  9. customPurify (silica gel chromatography)
  10. washeluting with 1:1:0.4 CH2Cl2

Sources & evidence

ORD record
ord-3f5d0a575b4b40a7ae2bfafb7c9195b0
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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