Isopropanol → HCID 57831024, Verbindung

HRID 240316

Reaktionsgleichung

Reaktionsgleichung von HRID 240316
[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=O)[C:9]2=O)=[CH:5][CH:4]=1)[CH3:2].[NH2:14]/[C:15](/[C:20]#[N:21])=[C:16](\[NH2:19])/[C:17]#[N:18].CC([OH:25])C>>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:25])[C:8]3[C:9]([C:10]=2[CH:11]=1)=[N:14][C:15]([C:20]#[N:21])=[C:16]([C:17]#[N:18])[N:19]=3)[CH3:2]

Komponenten

4

Edukt 3

HCID 3776IsopropanolHCID 2723951DiaminomaleonitrileHCID 57831019HCID 57831019, Verbindung

Produkt 1

HCID 57831024HCID 57831024, Verbindung

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 29c (298 mg, 1.71 mmol) and diaminomaleonitrile (185 mg, 1.71 mmol) in iPrOH (17 ml) was stirred at 80° C. for 20 h. The solvent was evaporated under reduced pressure and the crude was purified by flash chromatography (CH2Cl2). The obtained product was purified by preparative HPLC, obtaining 32 as yellow solid as 7:3 regioisomeric mixture with the 7-ethyl analogue. 1H NMR (300 MHz, CDCl3): main product: δ 7.95 (d, 1H), 7.80 (m, 1H), 7.67 (bd, 1H), 2.83 (q, 2H), 1.33 (t, 3H); minority product: δ 7.89 (d, 1H), 7.89 (m, 1H), 7.56 (bd, 1H), 2.86 (q, 2H), 1.36 (t, 3H). ESI+MS: calcd for C15H8N4O: 260.26; found: 261.1 (MH+).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude was purified by flash chromatography (CH2Cl2)
  3. customThe obtained product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2ecba929284b42688b3bc34e18d072dc
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648076B2

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