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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
Notes
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Reaction equation

HRID 253284 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-77dd8ce7a56d4542b6ea11f7550b2848
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07872014B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes