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

HRID 452977

反応式

HRID 452977 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™ (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-a1fb895377e843209297d16749b98ef0
出典データセット
uspto-grants-2013_07
特許番号
US08492371B2

関連ノート

読み込み中…