Water → HCID 38024052, compound

HRID 1178084Notes

Reaction equation

HRID 1178084 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:11]=[C:12]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH2:13][NH:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)=[O:16].O>C(Cl)Cl>[C:1]1([S:7]([N:32]2[CH2:31][CH2:30][N:29]([C:12](=[O:11])[CH2:13][NH:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:19][CH:18]=3)=[O:16])[CH2:34][CH2:33]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 57855677Biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide

Product 1

HCID 38024052HCID 38024052, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (62.57 mg, 062 mmol) followed by benzenesulphonyl chloride (54.6 mg, 0.31 mmol) were added at to 0° C. to biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide (100 mg, 0.31 mmol) in DCM (4 mL). The resulting mixture was stirred at room temperature overnight. Cold water was then added and the product extracted with DCM. The organic layer was separated, washed with 10% HCl solution, saturated NaHCO3 solution and brine, dried over sodium sulphate and concentrated. The resulting residue was purified by column chromatography (using 60-120 mesh silica gel and 30% EtOAc in hexane as eluent) to afford 45 mg (31.4% yield) of biphenyl-4-carboxylicacid {2-[4-benzene sulfonyl-piperazin-1-yl]-2-oxo-ethyl}-amide, LC-MS purity: 98.75%, 1H NMR: (DMSO) δ 8.76 (t, 1H), 7.92 (d, 2H), 7.8-7.6 (m, 9H), 7.54-7.44 (t, 2H), 7.44-7.36 (t, 1H), 4.1 (d, 2H), 3.6 (s, 4H), 3.0-2.86 (d, 4H).

Workup

  1. extractionthe product extracted with DCM
  2. customThe organic layer was separated
  3. washwashed with 10% HCl solution, saturated NaHCO3 solution and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography (using 60-120 mesh silica gel and 30% EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-c229d75aac83436cb8dd7327e8fd7d3d
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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