Phenylacetic Acid → HCID 25164322, compound

HRID 1177953Notes

Reaction equation

HRID 1177953 reaction equation
CCN(C(C)C)C(C)C.OC(C(F)(F)F)=O.[NH2:17][CH2:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:36])[F:35])[CH2:23][CH2:22]1)=[O:20].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:61]1([CH2:67][C:68](O)=[O:69])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>CN(C=O)C.O>[O:20]=[C:19]([N:21]1[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:35])[F:36])[CH2:25][CH2:26]1)[CH2:18][NH:17][C:68](=[O:69])[CH2:67][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

8

Reactant 5

HCID 999Phenylacetic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

Product 1

HCID 25164322HCID 25164322, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (68 mg, 0.53 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt (76 mg, 0.18 mmol) in DMF (1 mL). HOBT (24 mg, 0.18 mmol) and EDCI.HCl (34 mg, 0.18 mmol) were then added at room temperature. After 2 minutes, phenyl acetic acid (20 mg, 0.15 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water (20 mL) was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. the resulting residue was purified by column chromatography (using silica gel 60-120 mesh and 1% methanol in chloroform as eluent) to afford 28 mg (43.7% yield) of N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-2-phenyl-acetamide. LCMS Purity: 94.1%, 1H NMR (CDCl3): δ 7.8-7.7 (d, 1H). 7.6 (m, 2H), 7.4-7.2 (m, 5H), 6.5 (bd, 1H), 4.1 (m, 1H), 4.0 (m, 2H), 3.8 (m, 1H), 3.8-3.4 (m, 6H), 3.3 (t, 1H), 3.2-3.1 (m, 2H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue was purified by column chromatography (using silica gel 60-120 mesh and 1% methanol in chloroform as eluent)

Sources & evidence

ORD record
ord-a5fa70652f2347099c29e50f3f8071ab
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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