Dimethylformamide → HCID 67077935, compound

HRID 2088973Notes

Reaction equation

HRID 2088973 reaction equation
[H-].[Na+].CI.[Br:5][C:6]1[CH:11]=[N:10][C:9]2[N:12]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:13]=[CH:14][C:8]=2C=1N.[CH3:26][N:27]([CH3:30])[CH:28]=O>>[Br:5][C:6]1[CH:11]=[N:10][C:9]2[N:12]([S:15]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)(=[O:17])=[O:16])[CH:13]=[CH:14][C:8]=2[C:28]=1[N:27]([CH3:30])[CH3:26]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67078609HCID 67078609, compound

Product 1

HCID 67077935HCID 67077935, compound

Procedure

55% Sodium hydride (19 mg) and methyl iodide (0.027 ml) were added to a solution of the compound obtained in Step 2 of Example 130 (64 mg) in N,N-dimethylformamide (3.6 ml) in an ice bath, and the mixture was stirred in an ice bath for 2 hours. The reaction solution was separated by adding an aqueous ammonium chloride solution and ethyl acetate. The resulting organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (73 mg).

Workup

  1. customThe reaction solution was separated
  2. additionby adding an aqueous ammonium chloride solution and ethyl acetate
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane)

Sources & evidence

ORD record
ord-adaa409cc32546038312469f0426013a
Source dataset
uspto-grants-2013_05
Patent number
US08436012B2

Reaction notes

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