4-Phenoxybenzoic acid → HCID 25164521, compound

HRID 1177956Notes

Reaction equation

HRID 1177956 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.[O:61]([C:68]1[CH:76]=[CH:75][C:71]([C:72](O)=[O:73])=[CH:70][CH:69]=1)[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=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:72](=[O:73])[C:71]1[CH:70]=[CH:69][C:68]([O:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[CH:76][CH:75]=1

Participants

8

Reactant 5

HCID 751824-Phenoxybenzoic 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 25164521HCID 25164521, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (45 mg, 0.35 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt. (60 mg, 0.14 mmol) in DMF (1 mL). HOBT (19 mg, 0.14 mmol) and EDCI.HCl (27 mg, 0.14 mmol) were then added at room temperature. After 2 minutes, 4-phenoxybenzoic acid (25 mg, 0.12 mmol) was added 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 to afford 35 mg (58.3% yield) of N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-phenoxy-benzamide. LCMS Purity: 90.02%, HPLC Purity: 92.82%, 1H NMR (CDCl3): δ 7.8 (dd, 2H), 7.8-7.7 (dd, 1H), 7.6 (m, 2H), 7.4-7.3 (m, 3H), 7.2-7.1 (t, 2H), 7.1-7.0 (m, 4H), 4.4-4.3 (dd, 1H), 4.3-4.2 (dd, 1H), 4.0 (m, 2H), 3.8-3.6 (m, 4H), 3.4 (t, 1H), 3.3-3.2 (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-bf4865b5648e4aac914bc62cf82d3107
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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