1-Hydroxybenzotriazole → N-{2-oxo-2-[4-(2-trifluoromethyl-phenylamino)-piperidin-1-yl]-ethyl}-4-phenylamino-benzamide

HRID 1093592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1093592
[C:1]1([NH:7][C:8]2[CH:20]=[CH:19][C:11]([C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.Cl.[NH:54]1[CH2:59][CH2:58][CH:57]([NH:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=2[C:67]([F:70])([F:69])[F:68])[CH2:56][CH2:55]1>CN(C=O)C.O>[O:18]=[C:16]([N:54]1[CH2:55][CH2:56][CH:57]([NH:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=2[C:67]([F:68])([F:69])[F:70])[CH2:58][CH2:59]1)[CH2:15][NH:14][C:12](=[O:13])[C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:20][CH:19]=1

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57874498(4-Phenylamino-benzoylamino)-acetic acidHCID 66591440Piperidin-4-yl-(2-trifluoromethyl-phenyl)-amine dihydrochloride

Produkt 1

HCID 57874508N-{2-oxo-2-[4-(2-trifluoromethyl-phenylamino)-piperidin-1-yl]-ethyl}-4-phenylamino-benzamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of (4-phenylamino-benzoylamino)-acetic acid (0.058 g, 0.00021 mol) in DMF (5 mL) was added DIPEA (0.069 g, 0.00054 mol), HOBt (0.028 g, 0.0002142 mol) and EDCI.HCl (0.085 g, 0.00045 mol) at ambient temperature. After 2 minutes piperidin-4-yl-(2-trifluoromethyl-phenyl)-amine dihydrochloride (0.050 g, 0.00019 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was collected, washed with brine solution, dried over sodium sulfate and concentrated under reduced. The resulting residue was purified by column chromatography using silica gel 60-120 mesh (60% ethyl acetate in hexane) to afford 0.06 g (68%) of N-{2-oxo-2-[4-(2-trifluoromethyl-phenylamino)-piperidin-1-yl]-ethyl}-4-phenylamino-benzamide. LCMS: 497.21 (M+1)+, 95.3%, 1H NMR (DMSO-d6): δ 8.6 (s, 1H), 8.2 (t, 1H), 7.8 (d, 2H), 7.4 (m, 4H), 7.2 (d, 2H), 7.1 (m, 3H), 6.9 (t, 1H), 6.7 (t, 1H), 4.7 (d, 1H), 4.3 (d, 1H), 4.1 (s, 2H), 3.9 (d, 1H), 3.7 (s, 1H), 2.8 (t, 1H), 2.0 (t, 2H), 1.5 (m, 2H).

Aufarbeitung

  1. extractionthe product was extracted with ethyl acetate
  2. customThe ethyl acetate layer was collected
  3. washwashed with brine solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5a3fa0eadb48495790444d970e58f06c
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129376B2

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