Dimethylformamide → HCID 58706639, compound

HRID 1716500Notes

Reaction equation

HRID 1716500 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:18][CH2:17][NH:16][C:15](=[O:19])[CH2:14]3)=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:20]N(C)C=O.[H-].[Na+].CI>O1CCCC1.O>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:18][CH2:17][N:16]([CH3:20])[C:15](=[O:19])[CH2:14]3)=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58706495HCID 58706495, compound

Product 1

HCID 58706639HCID 58706639, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[5-(6-bromopyridin-2-yl)thiazol-2-yl]piperazin-2-one obtained in Step 4 (200 mg, 0.59 mmol) was dissolved in tetrahydrofuran (2 ml) and N,N-dimethylformamide (2 ml) and after sodium hydride (60% oily, 26 mg, 0.65 mmol) was added, methyl iodide (39 μl, 0.62 mmol) was added and the mixture was stirred overnight at room temperature. Water was added to the reaction solution and the residue obtained by vacuum concentration was extracted with ethyl acetate and washed with a saturated brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to give the title compound (188 mg, 90%).

Workup

  1. customthe residue obtained by vacuum concentration
  2. extractionwas extracted with ethyl acetate
  3. washwashed with a saturated brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d25b956185b4b7c847b7ef699a65293
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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