1-Hydroxybenzotriazole → HCID 57874499, Verbindung

HRID 1093702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1093702
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:16])[CH2:12][C:13]([OH:15])=O)[CH2:7][CH2:6]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[O:43]1[CH:47]=[N:46][C:45]([C:48]2[CH:53]=[CH:52][C:51]([NH2:54])=[CH:50][CH:49]=2)=[N:44]1>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11](=[O:16])[CH2:12][C:13]([NH:54][C:51]2[CH:50]=[CH:49][C:48]([C:45]3[N:46]=[CH:47][O:43][N:44]=3)=[CH:53][CH:52]=2)=[O:15])[CH2:9][CH2:10]1

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 214837044-(1,2,4-Oxadiazol-3-yl)anilineHCID 578744033-[4-(2-Chloro-phenoxy)-piperidin-1-yl]-3-oxo-propionic acid

Produkt 1

HCID 57874499HCID 57874499, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-3-oxo-propionic acid (0.1 g, 0.00034 mole) in DMF (2 mL) was added DMAP (0.063 g, 0.00051 mole), HOBt (0.055 g, 0.00041 mole) and EDCI.HCl (0.079 g, 0.00041 mole). After 2 minutes 4-[1, 2, 4]-oxadiazol-3-yl-phenylamine (0.06 g, 0.00037 mole) 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 dried over sodium sulfate and concentrated under reduced pressure to afford 0.09 g (61%) of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-N-(4-[1,2,4]oxadiazol-3-yl-phenyl)-3-oxo-propionamide. LC-MS purity: 441 (M+1)+, 94.4%, 1H NMR (CDCl3): δ 10.5 (s, 1H), 8.8 (s, 1H), 8.1 (d, 2H), 7.74 (d, 2H), 7.4 (d, 1H), 7.2 (d, 1H), 6.96 (t, 2H), 4.7 (q, 1H), 4.1 (m, 1H), 3.8 (m, 1H), 3.6 (m, 2H), 3.55 (s, 2H), 2.0 (m, 5H).

Aufarbeitung

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5de2b33eee0a4b599f217631ef985cfe
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129376B2

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