Acetonitrile → 2,2-Dimethylpropyl 4-{4-[5-(methylthio)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}-1-piperazinecarboxylate

HRID 421833Notes

Reaction equation

HRID 421833 reaction equation
[NH2:1][C:2](=[N:23][OH:24])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)[CH:4]=1.[C:25](N1C=CN=C1)(N1C=CN=C1)=[S:26].[C:37](#N)C>C(OCC)(=O)C>[CH3:37][S:26][C:25]1[O:24][N:23]=[C:2]([C:3]2[CH:8]=[CH:7][N:6]=[C:5]([N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:16])[CH2:11][CH2:10]3)[CH:4]=2)[N:1]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 802641,1'-ThiocarbonyldiimidazoleHCID 1363817182,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}-1-piperazinecarboxylate

Product 1

HCID 119928972,2-Dimethylpropyl 4-{4-[5-(methylthio)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}piperazine-1-carboxylate (340 mg) obtained in Example 26-1) was dissolved in acetonitrile (2 mL), and 1,1′-thiocarbonyldiimidazole (231 mg) was added thereto and stirred at room temperature for 2 hours. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was dissolved in dimethylformamide (2 mL), and methyl iodide (0.080 mL) and potassium carbonate (198 mg) were added thereto and stirred at room temperature for 1 hour. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=7/3) to obtain 25.2 mg of the entitled compound as a colorless oil.

Workup

  1. customThe reaction liquid
  2. washwashed with water and saturated saline water
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was evaporated away
  5. dissolutionthe resulting residue was dissolved in dimethylformamide (2 mL)
  6. additionmethyl iodide (0.080 mL) and potassium carbonate (198 mg) were added
  7. stirringstirred at room temperature for 1 hour
  8. customThe reaction liquid
  9. washwashed with water and saturated saline water
  10. dry with materialdried with anhydrous sodium sulfate
  11. customThe solvent was evaporated away
  12. customthe resulting residue was isolated
  13. custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-038f7c04242c4556914b1aae25b929a8
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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