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

HRID 717253

반응식

HRID 717253 반응식
[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]

참가 물질

7

반응물 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 178484244HCID 178484244, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 6225Tetraethylammonium Iodide촉매HCID 67553Tetrabutylammonium Iodide촉매HCID 94433Tetrabutylammonium hydrogen sulfate촉매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-94790b9ad81e42a0b6f73d231cea1879
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193713B2

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