Triethylamine → HCID 25167326, compound

HRID 1177947Notes

Reaction equation

HRID 1177947 reaction equation
CCN(CC)CC.[NH2:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:29])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:27])[F:26])[CH2:14][CH2:13]1)=[O:11].[C:30]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>C(Cl)Cl.O>[O:11]=[C:10]([N:12]1[CH2:13][CH2:14][N:15]([C:18](=[O:29])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:26])[F:27])[CH2:16][CH2:17]1)[CH2:9][NH:8][S:36]([C:33]1[CH:32]=[CH:31][C:30]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:35][CH:34]=1)(=[O:38])=[O:37]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 595596292-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone

Product 1

HCID 25167326HCID 25167326, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

Et3N (42 mg, 0.42 mmol) was added to a stirred solution of 2-amino-1[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone (80 mg, 0.19 mmol) in DCM (4 mL) at 0-5° C. 4-biphenylsulfonyl chloride (47 mg, 0.19 mmol) was then added and the mixture was stirred at 0-5° C. for 4 hrs. The reaction was then diluted with cold water and the product was extracted with DCM, washed with 5% NaHCO3, 5% HCl, then saturated brine solution. The DCM layer was dried over sodium sulphate and concentrated. The residue was purified by column chromatography (using silica gel of 60-120 mesh and 60% EtOAc in hexane as eluent) to afford 33 mg (33.4% yield) of biphenyl-4-sulfonicacid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LC-MS purity: 90.35%. 1H-NMR (CDCl3) δ 7.9 (m, 2H), 7.7 (d, 3H,), 7.6-7.5 (m 4H), 7.5-7.4 (m, 3H), 7.3 (m, 1H), 5.6 (s, 1H), 4.0-3.7 (m, 5H), 3.7-3.5 (m, 3H), 3.4-3.3 (m, 2H), 3.25-3.1 (m, 3H).

Workup

  1. extractionthe product was extracted with DCM
  2. washwashed with 5% NaHCO3, 5% HCl
  3. dry with materialThe DCM layer was dried over sodium sulphate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (using silica gel of 60-120 mesh and 60% EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-6cf18d763a02439291e472c2db6742b3
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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