Piperazin-2-one → HCID 19025734, compound

HRID 1974948Notes

Reaction equation

HRID 1974948 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:12][S:13](Cl)(=[O:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:24]=[C:25]1[CH2:30][NH:29][CH2:28][CH2:27][NH:26]1>ClCCl.N1C=CC=CC=1>[CH2:17]([CH:11]([CH2:12][S:13]([N:29]1[CH2:28][CH2:27][NH:26][C:25](=[O:24])[CH2:30]1)(=[O:15])=[O:14])[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 231360Piperazin-2-oneHCID 15018140HCID 15018140, compound

Product 1

HCID 19025734HCID 19025734, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To the resultant compound from Example 11C (320.5 mg, 0.908 mmol) in dichloromethane (5 mL) at -10° C. was added 2-oxopiperazine (140 mg, 1.40 mmol, Yu et al. J. Med. Chem. 1900, 31, 1435) in pyridine (2 mL). After 30 min at -10° C. and 30 min at ambient temperature, the solvent was evaporated and the residue was partitioned between ether and 0.5 M H3PO4. The organic layer was washed with 0.5 M H3PO4, saturated NaHCO3 solution and brine, and then was dried over MgSO4 and evaporated. Chromatography of the residue on silica gel with 2% methanol in chloroform afforded 237.1 mg (63%) of the desired product as a foam: TLC (5% methanol/95% chloroform) Rf =0.26; 1H NMR (CDCl3) 7.43-7.07 (m, 10H), 5.97 (br, 1H), 5.12 (d, 1H), 5.08 (d, 1H), 3.82 (d, 1H), 3.78 (d, 1H), 3.55 (dd, 1H), 3.43-3.17 (m, 5H), 3.07 (dd, 1H), 3.01 (dd, 1H), 2.87 (dd, 1H).

Workup

  1. custom30 min at ambient temperature, the solvent was evaporated
  2. customthe residue was partitioned between ether and 0.5 M H3PO4
  3. washThe organic layer was washed with 0.5 M H3PO4, saturated NaHCO3 solution and brine
  4. dry with materialwas dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-ebe15e920f804cf1b91532ea1c98f5bd
Source dataset
uspto-grants-1994_02
Patent number
US05284849

Reaction notes

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