2-Fluorobenzoic acid → N-biphenyl-4-yl-3-[4-(2-fluoro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide

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Reaktionsgleichung

C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=O.CCN=C=NCCCN(C)C.Cl.Cl.[C:43]1([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:48]=[CH:47][C:46]([NH:49][C:50](=[O:60])[CH2:51][C:52](=[O:59])[N:53]2[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]2)=[CH:45][CH:44]=1>CN(C=O)C.O>[C:43]1([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:44]=[CH:45][C:46]([NH:49][C:50](=[O:60])[CH2:51][C:52]([N:53]2[CH2:54][CH2:55][N:56]([C:23](=[O:25])[C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[F:20])[CH2:57][CH2:58]2)=[O:59])=[CH:47][CH:48]=1

Komponenten

Reaktionsbedingungen

Temperatur: 10 °C

Versuchsvorschrift

HOBt (34 mg, 0.25 mmol) and DIPEA (67.9 mg, 0.51 mmol) were added to a stirred solution of 2-fluorobenzoic acid (29 mg, 0.21 mmol) in DMF (1.5 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (48 mg, 0.25 mmol) followed by N-biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride (75 mg, 0.2 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water. The resulting precipitate was dried to afford 87 mg (94%) of N-biphenyl-4-yl-3-[4-(2-fluoro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide. LCMS: 446.18 (M+1)+ 93.2%, 1H NMR: (CDCl3): δ 9.7 (d, 1H), 7.6 (m, 6H), 7.44 (t, 4H), 7.34 (t, 1H), 7.22 (m, 1H), 7.14 (t, 1H), 3.86 (m, 6H), 3.54 (d, 2H), 3.4 (bs, 2H).

Aufarbeitung

additionwere added
customThe resulting precipitate was dried

Quellen und Nachweise

ORD-Eintrag: ord-70ce52a7bcb1407aba85d82456df6702
Quelldatensatz: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08039463B2

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