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

HRID 717253

反応式

HRID 717253 の反応式
[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]

参加物

7

反応物 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 178484244HCID 178484244、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 6225Tetraethylammonium Iodide触媒HCID 67553Tetrabutylammonium Iodide触媒HCID 94433Tetrabutylammonium hydrogen sulfate触媒

実験手順

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 T (SiO2, 0-10% methanol in dichloromethane) to provide 0.6 g (25%) of the title compound. MS (ESI+) m/z 293 (M+H)+.

後処理

  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

出典と根拠

ORDレコード
ord-94790b9ad81e42a0b6f73d231cea1879
出典データセット
uspto-grants-2015_11
特許番号
US09193713B2

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