2,4-Dimethylbenzoic acid → Biphenyl-4-carboxylicacid {2-[4-(2,4-dimethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide

HRID 1178012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178012
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.[CH3:63][C:64]1[CH:72]=[C:71]([CH3:73])[CH:70]=[CH:69][C:65]=1[C:66](O)=[O:67]>CN(C=O)C.O>[CH3:63][C:64]1[CH:72]=[C:71]([CH3:73])[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]

Komponenten

8

Edukt 5

HCID 118972,4-Dimethylbenzoic 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

Produkt 1

HCID 25166104Biphenyl-4-carboxylicacid {2-[4-(2,4-dimethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amideAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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 2,4-dimethylbenzoic acid (20 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 50 mg (82.4% yield) of biphenyl-4-carboxylicacid {2-[4-(2,4-dimethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LC-MS purity: 95.3%, 1H NMR: (CDCl3) δ 7.9 (d, 2H), 7.6 (dd, 4H), 7.5 (t, 2H), 7.35 (t, 1H), 7.3 (s, 1H), 7.0 (s, 3H), 4.4-4.2 (d, 2H), 3.9-

Aufarbeitung

  1. customthe product was precipitated
  2. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-4db6b5eb87514ac3bb7ed9d3cb74f26f
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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