Propionic Acid → HCID 66580430, Verbindung

HRID 1521873Notizen

Reaktionsgleichung

[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[C:15]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[S:22](=[O:25])(=[O:24])[CH2:23][C:14]=3[C:13]([C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])=[N:12]2)[CH:6]=1)[NH2:4].[C:34](O)(=O)[CH2:35][CH3:36]>CCOC(C)=O>[CH2:35]([C:36]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[C:7]([N:11]3[C:15]4[C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[S:22](=[O:24])(=[O:25])[CH2:23][C:14]=4[C:13]([C:26]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[O:27])=[N:12]3)[CH:8]=[CH:9][CH:10]=2)[N:4]=1)[CH3:34]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of N′-hydroxy-3-[3-(morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]benzenecarboximidamide (150 mg, 0.32 mmol) in dry EtOAc is added propionic acid (13 μl, 0.32 mmol) under nitrogen followed by TEA (0.13 mL, 0.963 mmol) and propane phosphonic acid cyclic anhydride (0.51 mL, 0.80 mmol) at 0° C. under nitrogen. The reaction mixture is heated to 80° C. for 12 h under nitrogen and concentrated under vacuum. Solid residue is purified by silica gel column chromatography (1.2% MeOH in DCM) to afford the title compound as an off white solid. 1H NMR (DMSO-d6, 400 MHz): δ 8.24-8.22 (d, J=7.4 Hz, 1H), 8.05-8.02 (m, 2H), 7.81-7.77 (m, 2H), 7.64 (m, 1H), 7.57 (m, 1H), 6.93-6.91 (d, J=7.9 Hz, 1H), 4.91 (s, 2H), 3.92-3.90 (m, 2H), 3.67 (m, 4H), 3.61-3.60 (m, 2H), 3.02-3.0 (m, 2H), 1.33-1.29 (t, J=7.6 Hz, 3H). MS (ESI+): 506.0. HPLC (max plot) 97.13%; Rt 4.34 min.

Aufarbeitung

concentrationconcentrated under vacuum
customSolid residue is purified by silica gel column chromatography (1.2% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag: ord-235733a77e0749a09e1dbc5a04b12a3e
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09073940B2

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