Methyl iodide → HCID 178481172, compound

HRID 1162363Notes

Reaction equation

HRID 1162363 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.[CH3:20]I>CN(C=O)C>[CH3:20][N:3]1[CH:4]=[CH:5][S:1]/[C:2]/1=[N:6]\[CH:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 231309421,1-Dimethylethyl 4-(2-thiazolylamino)-1-piperidinecarboxylate

Product 1

HCID 178481172HCID 178481172, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-(1,3-thiazol-2-yl)amino-1-piperidinecarboxylate (2.5 g) obtained in Example 135b) in DMF (50 ml) was added methyl iodide (1.1 ml), and mixed at 80° C. for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in chloroform and an aqueous potassium carbonate solution. The organic layer was collected by separation, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified with silica gel column to obtain the title compound as a pale yellow solid (0.54 g, 21%).

Workup

  1. additionmixed at 80° C. for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. customThe organic layer was collected by separation
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with silica gel column

Sources & evidence

ORD record
ord-22e9a938ba604d8d9a76c4816cd305ee
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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