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tert-Butylhydrazine monohydrochloride → 1-(1,1-dimethylethyl)-4-(5-fluoro-2-(methyloxy)-3-[{phenylmethyl)oxy]phenyl}-3-methyl-1H-pyrazol-5-amine

HRID 253284
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HRID 253284 반응식
[F:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]([O:14][CH3:15])=[C:6]([CH:8]([C:11](=O)[CH3:12])[C:9]#[N:10])[CH:7]=1.Cl.[C:25]([NH:29][NH2:30])([CH3:28])([CH3:27])[CH3:26]>C(O)C>[CH3:26][C:25]([N:29]1[C:9]([NH2:10])=[C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[C:4]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:5]=2[O:14][CH3:15])[C:11]([CH3:12])=[N:30]1)([CH3:28])[CH3:27]
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4

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HCID 81889tert-Butylhydrazine monohydrochlorideHCID 668904882-{5-Fluoro-2-(methyloxy)-3-[(phenylmethyl)oxy]phenyl}-3-oxobutanenitrile

생성물 1

HCID 668909321-(1,1-dimethylethyl)-4-(5-fluoro-2-(methyloxy)-3-[{phenylmethyl)oxy]phenyl}-3-methyl-1H-pyrazol-5-amine수율 98.3%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
75 °C

실험 절차

To a solution of 2-{5-fluoro-2-(methyloxy)-3-[(phenylmethyl)oxy]phenyl}-3-oxobutanenitrile (5.7 g, 18.1 mmol) in ethanol (60 mL) was added t-butylhydrazine hydrochloride (6.8 g, 54 mmol). The mixture was stirred for 2 h at 75° C. before cooling to rt and stirring for an additional 14 h. The volatile materials were removed in vacuo. To the residue was added water, and the resulting aqueous mixture was extracted with ethyl acetate 3 times. The organic extracts were combined and washed with 1 N HCl (aq) followed by aqueous NaHCO3 (sat). The organics were then dried over magnesium sulfate, filtered, and concentrated in vacuo to provide 1-(1,1-dimethylethyl)-4-{5-fluoro-2-(methyloxy)-3-[{phenylmethyl)oxy]phenyl}-3-methyl-1H-pyrazol-5-amine as a pale yellow syrup (6.81 g, 17.8 mmol, 98% yield). 1H NMR (400 MHz, CDCl3): δ 7.45-7.32 (m, 5H), 6.60 (dd, 1H), 6.53 (dd, 1H), 5.10 (s, 2H), 3.91 (br s, 2H), 3.55 (s, 3H), 2.20 (s, 3H), 1.67 (s, 9H); MS (EI) for C22H26FN3O2: 384 (MH+).

후처리

  1. temperaturebefore cooling to rt
  2. stirringstirring for an additional 14 h
  3. customThe volatile materials were removed in vacuo
  4. additionTo the residue was added water
  5. extractionthe resulting aqueous mixture was extracted with ethyl acetate 3 times
  6. washwashed with 1 N HCl (aq)
  7. dry with materialThe organics were then dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-77dd8ce7a56d4542b6ea11f7550b2848
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07872014B2

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