Dimethylformamide → HCID 18539194, compound

HRID 1394361Notes

Reaction equation

HRID 1394361 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:35][C:36]([NH2:38])=[O:37].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[C:18]([CH:20]2[CH2:21][CH2:22][N:23]([CH2:35][C:36](=[O:37])[NH2:38])[CH2:24][CH2:25]2)=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 18538605HCID 18538605, compound

Product 1

HCID 18539194HCID 18539194, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound obtained in Example 66 (391 mg, 0.80 mmol), 2-bromoacetamide (132 mg, 0.96 mmol), potassium carbonate (265 mg, 1.92 mmol) and DMF (5mL) was stirred at room temperature for 2 days. To the reaction mixture was added water (15 mL), and the mixture was extracted with ethyl acetate (15 mL×3). The organic layer was washed with water (5 mL×3), saturated sodium chloride solution (5 mL), successively, dried over, anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to column chromatography (silica gel 10 g, ethyl acetate/methanol=1/0 to 9/1), and the desired fraction was concentrated under reduced pressure to give the titled compound (357 mg, 0.65 mmol, Yield 82%) as a colorless oily substance.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (15 mL×3)
  2. washThe organic layer was washed with water (5 mL×3), saturated sodium chloride solution (5 mL)
  3. dry with materialsuccessively, dried over, anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b2dcb56f346b4346bd2c92532a980fa8
Source dataset
uspto-grants-2008_03
Patent number
US07348324B2

Reaction notes

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