2-Bromobenzoic acid → HCID 25165911, compound

HRID 1178020Notes

Reaction equation

HRID 1178020 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.[Br:63][C:64]1[CH:72]=[CH:71][CH:70]=[CH:69][C:65]=1[C:66](O)=[O:67]>CN(C=O)C.O>[Br:63][C:64]1[CH:72]=[CH:71][CH:70]=[CH:69][C:65]=1[C:66]([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:67]

Participants

8

Reactant 5

HCID 69402-Bromobenzoic 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 25165911HCID 25165911, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (144 mg, 1.11 mmol) was added to a stirred solution of biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide TFA salt (120 mg, 0.37 mmol) in DMF (5 mL). HOBT (60 mg, 0.45 mmol) and EDCI.HCl (178 mg, 0.93 mmol) were then added. After 2 minutes 2-bromobenzoic acid (89 mg, 0.45 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. Purification by column chromatography using silica gel 60-120 mesh and 80% EtOAc in hexane as eluent afforded 105 mg (56% yield) of biphenyl-4-carboxylic acid {2-[4-(2-bromo-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LC-MS purity: 96.78%, HPLC Purity: 97.31%. 1H NMR: (DMSO) δ 8.7 (t, 1H), 8.0 (d, 2H), 7.8 (m, 5H), 7.5 (m, 6H), 4.2 (dd, 2H), 3.6 (m, 6H), 3.2 (m, 2H).

Workup

  1. customthe product was precipitated
  2. filtrationfiltered
  3. customPurification by column chromatography

Sources & evidence

ORD record
ord-69cf999e593a48dbb121b4e6663f1e7b
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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