Acetic Acid → 5-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride

HRID 1174838노트

반응식

HRID 1174838 반응식
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].[ClH:10].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([NH:19][NH2:20])[CH:16]=[CH:17][CH:18]=1.C(O)(=O)C>C(O)C>[ClH:10].[C:2]([C:3]1[CH:4]=[C:5]([NH2:6])[N:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH3:11])[CH:14]=2)[N:20]=1)([CH3:9])([CH3:8])[CH3:1]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 27239403-Methoxyphenylhydrazine hydrochloride

생성물 1

HCID 670222745-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride수율 56%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 4,4-dimethyl-3-oxo-pentanenitrile (5.0 g, 40 mmol) and 3-methoxy-phenylhydrazine hydrochloride (7.0 g, 40 mmol) in anhydrous ethanol (200 mL) was added acetic acid (1.2 mL). The reaction mixture was heated at reflux overnight, then cooled to room temperature and concentrated at reduced pressure. The residue was combined with ethyl acetate (200 mL), and washed with saturated aq NaHCO3, water, and brine. The solution was dried over Na2SO4, evaporated at reduced pressure and the solid residue was re-dissolved in ethanol (100 mL). A solution of 2M HCl in ether was added and the mixture was stirred for 30 min. The solvent was removed at reduced pressure, the solid residue was triturated and washed with hexane (50 mL) and then dried in a vacuum oven overnight to give the product 5-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride (5.46 g, 56%) as an off-white solid. 1H-NMR (DMSO-d6) δ 7.50 (t, 1H), 7.10 (m, 3H), 5.60 (s, 1H), 3.80 (s, 3H), 1.30 (s, 9H); MS LC-MS [M+H]+=246.2, RT=1.90 min.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated at reduced pressure
  4. washwashed with saturated aq NaHCO3, water, and brine
  5. dry with materialThe solution was dried over Na2SO4
  6. customevaporated at reduced pressure
  7. dissolutionthe solid residue was re-dissolved in ethanol (100 mL)
  8. additionA solution of 2M HCl in ether was added
  9. customThe solvent was removed at reduced pressure
  10. customthe solid residue was triturated
  11. washwashed with hexane (50 mL)
  12. customdried in a vacuum oven overnight

출처 및 근거

ORD 기록
ord-a8c29e8fd3cb431489523a19923a7bc0
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838524B2

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