3-Phenoxybenzoic acid → HCID 25164319, compound

HRID 1178054Notes

Reaction equation

HRID 1178054 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 added at room temperature. After 2 minutes, 3-phenoxy-benzoic acid (40 mg, 0.19 mmol) was added. The resulting mixture was stirred at room temperature for four hours. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 70 mg (72.5% yield) of LCMS Purity %: 89.64, HPLC Purity %: 91.62, 1H NMR (DMSO-d6): δ 8.7-8.6 (bt, 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), 3.2-3 (m, 2H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford 70 mg (72.5% yield) of LCMS Purity %: 89.64, HPLC Purity %: 91.62, 1H NMR (DMSO-d6): δ 8.7-8.6 (bt, 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), 3.2-3 (m, 2H)

Sources & evidence

ORD record
ord-872694f0604742d2bd9f962f0f83bdb0
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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