(4-Fluorophenyl)hydrazine → HCID 9931377, compound

HRID 429355Notes

Reaction equation

HRID 429355 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
  8. washby flash chromatography (elution gradient: CH2Cl2—3%MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c20df03746864d28af6b123c6552e889
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

Loading…