Benzoic Acid → Biphenyl-4-carboxylicacid {2-[4-benzoyl-piperazin-1-yl]-2-oxo-ethyl}-amide

HRID 1178014Notes

Reaction equation

HRID 1178014 reaction equation
CCN(C(C)C)C(C)C.OC(C(F)(F)F)=O.[O:17]=[C:18]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[CH2:19][NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)=[O:22].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:63](O)(=[O:70])[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1>CN(C=O)C.O>[C:63]([N:38]1[CH2:39][CH2:40][N:35]([C:18](=[O:17])[CH2:19][NH:20][C:21]([C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:27][CH:28]=2)=[O:22])[CH2:36][CH2:37]1)(=[O:70])[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

Participants

8

Reactant 5

HCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131728551biphenyl-4-carboxylic acid (2-oxo-2-piperazin-1-yl-ethyl)-amide TFA salt

Product 1

HCID 25166103Biphenyl-4-carboxylicacid {2-[4-benzoyl-piperazin-1-yl]-2-oxo-ethyl}-amideYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (77.35 mg, 0.60 mmol) was added to a stirred solution of biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide TFA salt (70 mg, 0.16 mmol) in DMF (2 mL). HOBT (19.8 mg, 0.14 mmol) and EDCI.HCl (63.74 mg, 0.33 mmol) were then added. After 2 minutes benzoic acid (16.35 mg, 0.13 mmol) was added and the resulting mixture was stirred overnight. The reaction mixture was diluted with cold water and the product was precipitated and filtered to afford 40 mg (67.2% yield) of biphenyl-4-carboxylicacid {2-[4-benzoyl-piperazin-1-yl]-2-oxo-ethyl}-amide. LC-MS purity: 92.6%, 1H NMR Values: (CDCl3) δ 7.9 (d, 2H), 7.7 (d, 2H), 7.6 (d, 2H), 7.5-7.4 (m, 8H), 7.3 (s, 1H), 4.4 (s, 2H), 3.8 (s, 4H), 3.6 (s, 4H).

Workup

  1. customthe product was precipitated
  2. filtrationfiltered

Sources & evidence

ORD record
ord-16c2566ef93c48f7a5ff4b89f8da9706
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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