3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole → HCID 18407256, compound

HRID 1016607Notes

Reaction equation

HRID 1016607 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[C:19]([O:23][C:24]([N:26]1[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C1(C)C=CC=CC=1>[C:19]([O:23][C:24]([NH:26][CH2:27][CH2:28][N:10]1[CH2:11][CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazoleHCID 15933185tert-Butyl aziridine-1-carboxylate

Product 1

HCID 18407256HCID 18407256, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Part A: A stirred solution of 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (5.00 gram, 19.5 mmol) and N-(tert-butoxycarbonyl)aziridine (2.00 gram, 14.0 mmol) in toluene (100 ml) was heated at reflux temperature for 16 hours. After concentration in vacuo the residue was purified by flash chromatography (petroleum ether/diethyl ether=3/1 (v/v)), followed by petroleum ether/diethyl ether=1/1 (v/v)). After concentration in vacuo the remaining oily residue was crystallised from diisopropyl ether to afford 1-[2-((tert-butoxycarbonyl)amino)ethyl]-3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (1.91 gram, 34%). Repeated crystallisations from the mother liquor afforded an additional amount of crystalline 1-[2-((tert-butoxycarbonyl)amino)ethyl]-3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (1.19 gram).

Workup

  1. temperatureat reflux temperature for 16 hours
  2. concentrationAfter concentration in vacuo the residue
  3. customwas purified by flash chromatography (petroleum ether/diethyl ether=3/1 (v/v))
  4. concentrationAfter concentration in vacuo the remaining oily residue
  5. customwas crystallised from diisopropyl ether

Sources & evidence

ORD record
ord-2be5056a349d4cfbaba3a020fcc6b36b
Source dataset
uspto-grants-2002_11
Patent number
US06476060B2

Reaction notes

Loading…