Potassium Carbonate → HCID 66580801, Verbindung

HRID 1521874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521874
[N:1]1([C:7]([C:9]2[C:10]3[CH2:29][S:28](=[O:31])(=[O:30])[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:11]=3[N:12]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[C:17]#[N:18])[N:13]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:32]([N:35]=[N+:36]=[N-])(=O)[CH3:33].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[CH3:33][C:32]1[NH:35][N:36]=[C:17]([C:16]2[CH:15]=[C:14]([N:12]3[C:11]4[C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=5[S:28](=[O:30])(=[O:31])[CH2:29][C:10]=4[C:9]([C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:8])=[N:13]3)[CH:21]=[CH:20][CH:19]=2)[N:18]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12841679Acetyl azideHCID 68228419HCID 68228419, Verbindung

Produkt 1

HCID 66580801HCID 66580801, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 3-[3-(morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]benzonitrile (100 mg, 0.23 mmol) in dry toluene is added acetic azide (34 mg, 0.46 mmol) and K2CO3 (158 mg, 0.115 mmol) under nitrogen. The reaction mixture is heated to 110° C. for 12 h under nitrogen after which it is concentrated under vacuum. The solid residue is purified by Preparative HPLC to afford the title compound as an off white solid. 1H NMR (DMSO-d6, 400 MHz): δ 8.21-8.19 (d, J=7.7 Hz, 1H), 8.03-7.98 (m, 2H), 7.73-7.69 (m, 1H), 7.64-7.56 (m, 3H), 6.92-6.90 (d, J=7.8 Hz, 1H), 4.91 (s, 2H), 3.93 (m, 2H),3.75-3.67 (m, 4H), 3.62-3.61 (m, 2H), 2.37 (s, 3H). MS (ESI+): 491.0. HPLC (max plot) 98.76%; Rt 2.96 min.

Aufarbeitung

  1. concentrationis concentrated under vacuum
  2. customThe solid residue is purified by Preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d83ebb1b0f034a5c925744e344cacea5
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073940B2

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