2,4-Dichlorobenzoic Acid → N-{2-[4-(2,4-Dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide

HRID 1178039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178039
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[O:43]=[C:44]([N:62]1[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1)[CH2:45][NH:46][C:47](=[O:61])[C:48]1[CH:53]=[CH:52][C:51]([O:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[CH:50][CH:49]=1>CN(C=O)C.O>[Cl:10][C:11]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:12]=1[C:13]([N:65]1[CH2:66][CH2:67][N:62]([C:44](=[O:43])[CH2:45][NH:46][C:47](=[O:61])[C:48]2[CH:49]=[CH:50][C:51]([O:54][C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)=[CH:52][CH:53]=2)[CH2:63][CH2:64]1)=[O:15]

Komponenten

8

Edukt 5

HCID 57872,4-Dichlorobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66953134N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide hydrochloride

Produkt 1

HCID 59559574N-{2-[4-(2,4-Dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (0.11 mL, 0.64 mmol) was added drop wise to 2,4-dichlorobenzoic acid (48 mg, 0.26 mmol) in DMF (5 mL). EDCI (102 mg, 0.53 mmol) and HOBT (34 mg, 0.26 mmol) were added consecutively. After 10 mins, N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide hydrochloride (80 mg, 0.21 mmol) was added and the resulting mixture was stirred at room temperature overnight. 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 the crude product. Purification using column chromatography (silica gel of mesh size of 60-120 using 60:40 EtOAc:hexane as eluent) afforded N-{2-[4-(2,4-Dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide: in 64% yield. LC-MS purity: 97%, 1H NMR (DMSO-D6): δ 8.5 (t, 1H), 7.9 (d, 2H), 7.7 (s, 1H), 7.5 (m, 4H), 7.2 (t, 1H), 7.1 (m, 4H), 4.2 (dd, 2H), 3.6 (m, 4H), 3.5 (m, 2H), 3.2 (m, 2H).

Aufarbeitung

  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 the crude product
  6. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-9b9b83dbe91f460e9e3240a9d982c9d9
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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