Methyl iodide → HCID 11157562, compound

HRID 1455666Notes

Reaction equation

HRID 1455666 reaction equation
[CH3:1][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([C:24]4[CH:25]=[CH:26][C:27](=[O:40])[NH:28][C:29]=4[C:30]4[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=4)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:3].[H-].[Na+].[CH3:43]I>CN(C=O)C.[NH4+].[Cl-]>[CH3:43][N:28]1[C:29]([C:30]2[CH:31]=[CH:32][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:34][CH:35]=2)=[C:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:16]3[CH:17]=[C:8]([C:2]([CH3:1])([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:3])[CH:9]=[C:10]4[C:15]=3[N:14]=[CH:13][CH:12]=[CH:11]4)[CH:19]=2)[CH:25]=[CH:26][C:27]1=[O:40]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11433093HCID 11433093, compound

Product 1

HCID 11157562HCID 11157562, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of EXAMPLE 158 in DMF (0.05M) at 0° C. was added NaH (1.1 eq) followed by MeI (6 eq). The reaction mixture was stirred at rt for 1 h, diluted with NH4Cl solution and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (hexane:EtOAc, 70:30, then EtOH:EtOAc, 12:88) to afforded the title compound and EXAMPLE 160.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (hexane

Sources & evidence

ORD record
ord-d65843c9a9a4446481a54f39abea4998
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

Loading…