Toluene → N'-[3-tert-butyl-1-[[(5R)-5-methyloxolan-2-yl]methyl]pyrazol-5-yl]-N,N-dimethylmethanimidamide

HRID 452977

Reaction equation

HRID 452977 reaction equation
[C:1]([C:5]1[CH:9]=[C:8](/[N:10]=[CH:11]/[N:12]([CH3:14])[CH3:13])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-:16].[K+].[K+].[C:21]1(C)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].C([N+](CC)(CC)CC)C.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([C:5]1[CH:9]=[C:8](/[N:10]=[CH:11]/[N:12]([CH3:14])[CH3:13])[N:7]([CH2:21][CH:22]2[CH2:23][CH2:24][C@@H:25]([CH3:26])[O:16]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 178484244HCID 178484244, compound

Product 1

HCID 87439811N'-[3-tert-butyl-1-[[(5R)-5-methyloxolan-2-yl]methyl]pyrazol-5-yl]-N,N-dimethylmethanimidamideYield 25%

Reagents, catalysts & solvents 3

HCID 6225Tetraethylammonium IodideCatalystHCID 67553Tetrabutylammonium IodideCatalystHCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

To a solution of Example 63A (1.6 g, 8.2 mmol) in toluene (100 mL) were added potassium carbonate (2.3 g, 16.5 mmol), Example 64B (2.7 g, 9.9 mmol), tetrabutylammonium iodide (70 mg), tetraethylammonium iodide (70 mg) and tetrabutylammonium hydrogensulfate (70 mg). The reaction mixture was refluxed for 16 h, cooled, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-10% methanol in dichloromethane) to provide 0.6 g (25%) of the title compound. MS (ESI+) m/z 293 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a1fb895377e843209297d16749b98ef0
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Linked notes

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