4-Benzoylbenzoic acid → HCID 25164320, compound

HRID 1177950Notes

Reaction equation

HRID 1177950 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]([C:69]1[CH:77]=[CH:76][C:72]([C:73](O)=[O:74])=[CH:71][CH:70]=1)(=[O:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>CN(C=O)C.O>[C:61]([C:69]1[CH:70]=[CH:71][C:72]([C:73]([NH:17][CH2:18][C:19](=[O:20])[N:21]2[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:35])[F:36])[CH2:25][CH2:26]2)=[O:74])=[CH:76][CH:77]=1)(=[O:68])[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

Participants

8

Reactant 5

HCID 691474-Benzoylbenzoic 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 25164320HCID 25164320, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (77 mg, 0.103 mL, 0.60 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt (102 mg, 0.29 mmol) in DMF (1 mL). HOBT (32 mg, 0.29 mmol) and EDCI.HCl (46 mg, 0.29 mmol) were then added at room temperature. After 2 minutes, 4-benzoylbenzoic acid (45 mg, 0.20 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water 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 to afford 54 mg (51.9% yield) of 4-benzoyl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity %: 91.57, HPLC Purity: 95.52%, 1H NMR (DMSO-d6): δ 8.8 (t, 1H), 8.1-8.0 (d, 2H), 7.9-7.64 (m, 7H), 7.6 (t, 3H), 4.3-4.1 (m, 2H), 3.8-3.5 (m, 4H), 3.5-3.4 (m, 2H), 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

Sources & evidence

ORD record
ord-bb0cffb9991d47f8a8e8ddec61029938
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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