1-Hydroxybenzotriazole → 1'-{[3,5-Diethoxy-4-(1H-pyrazol-4-yl)phenyl]carbonyl}-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one

HRID 1096892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096892
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:23]([O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:40][CH2:41][CH3:42])[C:34]=1[C:35]1[CH:36]=[N:37][NH:38][CH:39]=1)[C:29]([OH:31])=O)[CH3:24].Cl.[O:44]=[C:45]1[O:49][N:48]=[C:47]([C:50]2[CH:51]=[C:52]3[C:62](=[CH:63][CH:64]=2)[O:61][C:55]2([CH2:60][CH2:59][NH:58][CH2:57][CH2:56]2)[CH2:54][C:53]3=[O:65])[NH:46]1>O.CN(C=O)C.CCN(CC)CC>[CH2:41]([O:40][C:33]1[CH:32]=[C:28]([C:29]([N:58]2[CH2:59][CH2:60][C:55]3([CH2:54][C:53](=[O:65])[C:52]4[C:62](=[CH:63][CH:64]=[C:50]([C:47]5[NH:46][C:45](=[O:44])[O:49][N:48]=5)[CH:51]=4)[O:61]3)[CH2:56][CH2:57]2)=[O:31])[CH:27]=[C:26]([O:25][CH2:23][CH3:24])[C:34]=1[C:35]1[CH:36]=[N:37][NH:38][CH:39]=1)[CH3:42]

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667819963,5-diethoxy-4-(1H-pyrazol-4-yl)benzoic acidHCID 1363426496-(5-Oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one hydrochloride

Produkt 1

HCID 1359101721'-{[3,5-Diethoxy-4-(1H-pyrazol-4-yl)phenyl]carbonyl}-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Et3N (83 μL), HOBT (46 mg) and WSC hydrochloride (58 mg) were added to a DMF (4 mL) solution of 3,5-diethoxy-4-(1H-pyrazol-4-yl)benzoic acid (101 mg) and 6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (70 mg), and stirred overnight at room temperature. Water was added to the reaction liquid, the formed solid was taken out through filtration, and the solid was washed with water and ether. The solid was dried under reduced pressure to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 12.96 (1H, s), 8.21 (1H, d, J=4.0 Hz), 8.06 (2H, s), 8.00 (11, dd, J=8.0, 4.0 Hz), 7.30 (1H, d, J=8.0 Hz), 6.68 (2H, s), 4.32-4.18 (1H, m), 4.08 (4H, q, J=8.0 Hz), 3.64-3.20 (3H, m), 2.97 (2H, s), 2.10-1.75 (4H, m), 1.37 (6H, t, J=8.0 Hz). MS [M+H]+=560.

Aufarbeitung

  1. filtrationthe formed solid was taken out through filtration
  2. washthe solid was washed with water and ether
  3. customThe solid was dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3c51355488234bebb9e7172f8d475483
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138197B2

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