Dimethylformamide → HCID 86642083, compound

HRID 1967418Notes

Reaction equation

HRID 1967418 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Cl:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=1[C:27]1[NH:32][C:31](=[O:33])[C:30]2=[C:34]([CH:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH:35]=[C:36]([CH3:37])[N:29]2[N:28]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=1[C:27]1[N:32]([CH2:2][C:3]([O:5][CH3:6])=[O:4])[C:31](=[O:33])[C:30]2=[C:34]([CH:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH:35]=[C:36]([CH3:37])[N:29]2[N:28]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 136042278HCID 136042278, compound

Product 1

HCID 86642083HCID 86642083, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

Methyl bromoacetate (0.14 mL), potassium carbonate (66 mg) and tetrabutylammonium iodide (12 mg) were added to the N,N-dimethylformamide solution (3 mL) of the compound prepared in Example 36 (109 mg), and the reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed by a saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (with an automatic purifying equipment made in Yamazen corporation) to obtain a title compound (95 mg) having the following physical data.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed by a saturated aqueous solution of sodium chloride
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe obtained residue was purified by column chromatography on silica gel (with an automatic purifying equipment

Sources & evidence

ORD record
ord-5dfcdb716f034121aa9d71229fe90885
Source dataset
uspto-grants-2013_04
Patent number
US08420810B2

Reaction notes

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