(4-Fluorophenyl)hydrazine → HCID 9931377, compound

HRID 843059Notes

Reaction equation

HRID 843059 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[N:10]1([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:41]=[CH:42][CH:43]=2)[C:22]([C:24]2[C:34](C3C=CC=CC=3)=CC=C[C:25]=2[NH:26]C(=C)C#N)=[O:23])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>C(O)C.O>[NH2:26][C:25]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=[CH:34][C:24]=1[C:22](=[O:23])[C:21]1[CH:41]=[CH:42][CH:43]=[C:19]([O:18][CH2:17][CH2:16][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[CH:20]=1

Participants

5

Reactant 2

HCID 69982(4-Fluorophenyl)hydrazineHCID 86757965HCID 86757965, compound

Product 1

HCID 9931377HCID 9931377, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-fluorophenylhydrazine (1.0 g, 6.8 mmol) and 2-[3-(2-morpholin-4-ylethoxy)-benzoyl]-3-phenylamlinoacrylonitrile (2.0 g, 5.3 mmol) in ethanol (30 ml) was heated at reflux under a nitrogen atmosphere. After 6 h, the reaction mixture was cooled to room temperature and diluted with water. The product was extracted into ethyl acetate and the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography (elution gradient: CH2Cl2-3%MeOH/CH2Cl2) gave 5-amino-1-(4-fluorophenyl)-4-[3-(2-morpholin-4-ylethoxy)benzoyl]pyrazole which was converted to the hydrochloride salt (0.7 g, mpt. 191.6-192.5° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere
  3. extractionThe product was extracted into ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification
  8. washby flash chromatography (elution gradient: CH2Cl2-3%MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-93db2b6073604425a0fed43d044f8a51
Source dataset
uspto-grants-2002_04
Patent number
US06376527B1

Reaction notes

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