Piperazin-2-one → HCID 19025734, compound

HRID 1033210Notes

Reaction equation

HRID 1033210 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 0.5M H3PO4. The organic layer was washed with 0.5M 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, 1 H), 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 0.5M H3PO4
  3. washThe organic layer was washed with 0.5M H3PO4, saturated NaHCO3 solution and brine
  4. dry with materialwas dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-d34d4b9729b94d9aada9d6582669104d
Source dataset
uspto-grants-1994_05
Patent number
US05310740

Reaction notes

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