Hydrazine, ethyl-, ethanedioate (1:1) → 4-(4-(2-Phenyleth-1-yl)-1-ethyl-(1h)-pyrazol-5-yl)-1-benzylpiperidine

HRID 1357893Notes

Reaction equation

HRID 1357893 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[CH:15]([CH:24]=O)[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C(O)=O.[CH2:33]([NH:35][NH2:36])[CH3:34]>CO>[C:18]1([CH2:17][CH2:16][C:15]2[CH:24]=[N:36][N:35]([CH2:33][CH3:34])[C:14]=2[CH:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 181877591-(1-Benzylpiperidin-4-yl)-2-formyl-4-phenylbutan-1-one

Product 1

HCID 181875714-(4-(2-Phenyleth-1-yl)-1-ethyl-(1h)-pyrazol-5-yl)-1-benzylpiperidineYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

di-TFA salt A solution of 1-(1-benzylpiperidin-4-yl)-2-formyl-4-phenyl-1-butanone from Step E (76.5 mg) and ethylhydrazine oxalate (45 mg) in methanol (4 mL) was heated at 45° C. for 15.5 h. The solvent was removed under reduced pressure. The residue was purified by preparative reverse-phase IHPLC using a 9.4×250 mm Semi-preparative Zorbax SB-C18 column with 30-50% acetonitrile gradient in water having 0.5% (v/v) TFA over 15 min at 7.1 mL per min to give the title compound (45 mg) as the faster-eluting, minor isomer.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by preparative reverse-phase
  3. customover 15 min

Sources & evidence

ORD record
ord-bef36d63bace412da1f6004a4cf71443
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

Loading…