3-Phenoxybenzoic acid → HCID 25164319, compound

HRID 1177949Notes

Reaction equation

HRID 1177949 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:69]=[C:70]([CH:74]=[CH:75][CH:76]=1)[C:71](O)=[O:72])[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:71](=[O:72])[C:70]1[CH:74]=[CH:75][CH:76]=[C:68]([O:61][C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[CH:69]=1

Participants

8

Reactant 5

HCID 195393-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 25164319HCID 25164319, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (73 mg, 0.097 mL, 0.56 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt (96 mg, 0.22 mmol) in DMF (1 mL). HOBT (30 mg, 0.22 mmol) and EDCI.HCl (43 mg, 0.22 mmol) were then added at room temperature. After 2 minutes, 3-phenoxybenzoic acid (40 mg, 0.19 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 70 mg (72.5% yield) of N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-3-phenoxy-benzamide. LCMS Purity: 89.64%. 1H NMR (DMSO-d6): δ 8.7-8.6 (t, 1H), 7.9-7.4 (m, 8H), 7.2 (m, 1H), 7.1-7.0 (d, 1H), 4.2-4.0 (m, 2H), 3.8-3.4 (m, 6H), 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-617525bebfa54bd28916a2e3dde15ea1
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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