(4-Fluorophenyl)hydrazine → HCID 9931377, compound

HRID 1278862Notes

Reaction equation

HRID 1278862 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:35]=[CH:36][CH:37]=2)[C:22]([C:24](=[CH:27]NC2C=CC=CC=2)[C:25]#[N:26])=[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:27][C:24]=1[C:22](=[O:23])[C:21]1[CH:35]=[CH:36][CH:37]=[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 67024295HCID 67024295, 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-phenylaminoacrylonitrile (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 by flash chromatography (
  8. washelution gradient

Sources & evidence

ORD record
ord-cd4a5f479f9f456ab174af5d63dd8ae4
Source dataset
uspto-grants-2002_09
Patent number
US06444696B1

Reaction notes

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