1-Hydroxybenzotriazole → HCID 178523501, Verbindung

HRID 1093608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1093608
[C:1]1([C:7]2[NH:11][N:10]=[C:9]([C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])[CH:8]=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.[N+:51]([C:54]1[CH:66]=[CH:65][CH:64]=[CH:63][C:55]=1[O:56][CH:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1)([O-:53])=[O:52]>CN(C=O)C.O>[N+:51]([C:54]1[CH:66]=[CH:65][CH:64]=[CH:63][C:55]=1[O:56][CH:57]1[CH2:62][CH2:61][N:60]([C:16](=[O:18])[CH2:15][NH:14][C:12]([C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:11][N:10]=2)=[O:13])[CH2:59][CH2:58]1)([O-:53])=[O:52]

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 467391574-(2-Nitrophenoxy)piperidine hydrochlorideHCID 178525878HCID 178525878, Verbindung

Produkt 1

HCID 178523501HCID 178523501, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.15 g, 0.0006 mol) in DMF (3 mL) was added DIPEA (0.27 g, 0.0021 mol), HOBt (0.12 g, 0.0009 mol) and EDCI.HCl (0.17 g, 0.0009 mol) at ambient temperature. After 2 minutes 4-(2-nitro-phenoxy)-piperidine hydrochloride (0.19 g, 0.00073 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water. The product was extracted with ethyl acetate, and the organic layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography using neutral aluminium oxide (5% methanol in chloroform) to afford 0.1 g (44%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-nitro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 450.17 (M+1)+, 96.5%, 1H NMR (DMSO-d6): δ 8.1 (bs, 1H), 7.9 (m, 3H), 7.6 (m, 1H), 7.5 (m, 4H), 7.1 (m, 2H), 5.0 (m, 1H), 4.2 (m, 2H), 3.8 (m, 8H), 2.0 (m, 2H).

Aufarbeitung

  1. extractionThe product was extracted with ethyl acetate
  2. washthe organic layer was washed with brine solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f25ae17f766d414da33af8fe818177cf
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129376B2

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