1-Hydroxybenzotriazole → HCID 178466811, Verbindung

HRID 1096896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096896
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][O:38][CH:39]=1)[C:29]([OH:31])=O)[CH3:24].Cl.[NH:44]1[C:48]([C:49]2[CH:50]=[C:51]3[C:61](=[CH:62][CH:63]=2)[O:60][C:54]2([CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)[CH2:53][C:52]3=[O:64])=[N:47][N:46]=[N:45]1>O.CN(C=O)C.CCN(CC)CC>[CH2:41]([O:40][C:33]1[CH:32]=[C:28]([C:29]([N:57]2[CH2:58][CH2:59][C:54]3([CH2:53][C:52](=[O:64])[C:51]4[C:61](=[CH:62][CH:63]=[C:49]([C:48]5[NH:47][N:46]=[N:45][N:44]=5)[CH:50]=4)[O:60]3)[CH2:55][CH2:56]2)=[O:31])[CH:27]=[C:26]([O:25][CH2:23][CH3:24])[C:34]=1[C:35]1[CH:36]=[N:37][O:38][CH:39]=1)[CH3:42]

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579309183,5-Diethoxy-4-isoxazol-4-yl-benzoic acidHCID 178479612HCID 178479612, Verbindung

Produkt 1

HCID 178466811HCID 178466811, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Et3N (104 μL), HOBT (57 mg) and WSC hydrochloride (71 mg) were added to a DMF (4 mL) solution of 3,5-diethoxy-4-isoxazol-4-yl-benzoic acid (86 mg) and 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (119 mg), and stirred overnight at room temperature. Water was added to the reaction liquid, the formed solid was taken out through filtration, and washed with water and ether. The resulting solid was purified through high-performance preparative liquid chromatography (0.1% TFA, water/acetonitrile) to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 9.18 (1H, s), 8.96 (1H, s), 8.42 (1H, d, J=4.0 Hz), 8.21 (1H, dd, J=8.0, 4.0 Hz), 7.33 (1H, d, J=8.0 Hz), 6.74 (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]+=545.

Aufarbeitung

  1. filtrationthe formed solid was taken out through filtration
  2. washwashed with water and ether
  3. customThe resulting solid was purified through high-performance preparative liquid chromatography (0.1% TFA, water/acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-c4cac8a3b4e34b99863e172aada83eeb
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138197B2

Notizen zur Reaktion

Wird geladen…