Dimethylformamide → HCID 56943752, compound

HRID 2387736Notes

Reaction equation

HRID 2387736 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].CI.CN(C=O)C.[CH3:14][C:15]1[N:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:23][C@@:24]2([C:37]3[CH:42]=[CH:41][C:40](O)=[C:39]([F:44])[CH:38]=3)[CH2:26][C@H:25]2[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][N:31]=2)=[O:28])=[CH:17][N:16]=1>O>[CH3:14][C:15]1[N:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:23][C@@:24]2([C:37]3[CH:42]=[CH:41][C:40]([O:4][CH3:1])=[C:39]([F:44])[CH:38]=3)[CH2:26][C@H:25]2[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][N:31]=2)=[O:28])=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 56943751HCID 56943751, compound

Product 1

HCID 56943752HCID 56943752, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cesium carbonate (172 mg) and methyl iodide (26.8 ul) were added to a DMF (5 ml) solution of the compound 321 (150 mg), and the obtained mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=9:1 to 2:3), so as to obtain the title compound (70 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=9:1 to 2:3)

Sources & evidence

ORD record
ord-83c48841387740be8f520911c793d733
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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