2-Acetylbenzoic acid → HCID 66953526, compound

HRID 1178083Notes

Reaction equation

HRID 1178083 reaction equation
CCN(C(C)C)C(C)C.[C:10]([C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=O)(=[O:12])[CH3:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[O:44]=[C:45]([N:62]1[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1)[CH2:46][NH:47][C:48]([C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[CH:52][CH:51]=1)=[O:49]>CN(C=O)C.O>[C:10]([C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([N:65]1[CH2:64][CH2:63][N:62]([C:45](=[O:44])[CH2:46][NH:47][C:48]([C:50]2[CH:55]=[CH:54][C:53]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)=[CH:52][CH:51]=2)=[O:49])[CH2:67][CH2:66]1)=[O:17])(=[O:12])[CH3:11]

Participants

8

Reactant 5

HCID 684742-Acetylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57855677Biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide

Product 1

HCID 66953526HCID 66953526, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (179.8 mg, 1.39 mmol) was added to the stirred solution of 2-acetyl-benzoic acid (50.75 mg, 0.31 mmol) in DMF (3 mL), HOBt (45.95 mg, 0.34 mmol) and EDCI.HCl (148.14 mg, 0.77 mmol) at room temperature. After 2 minutes biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide (120 mg, 0.37 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, and the resulting precipitate was filtered. The residue was purified by column chromatography (using 60-120 mesh silica gel and 50% EtOAc in hexane as eluent) to afford 30 mg (20.6% yield) of biphenyl-4-carboxylicacid {2-[4-(2-acetyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide, LC-MS purity: 95.52%, 1H NMR: (DMSO) δ 8.64 (s, 1H), 8.0 (dd, 3H), 7.84-7.72 (q, 4H), 7.7-7.64 (t, 1H), 7.6 (t, 1H), 7.5 (t, 2H), 7.44-7.32 (m, 2H), 4.26-4.1 (dd, 2H), 3.76-3.62 (d, 4H), 3.46 (s, 2H), 3.3 (d, 2H), 2.6 (s, 3H).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customThe residue was purified by column chromatography (using 60-120 mesh silica gel and 50% EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-56d72af43c624206b60a25846d86d1b5
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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