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Water → HCID 76577927, Verbindung

HRID 240319
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 240319
[C:1]([C:3]1[N:4]=[C:5]2[C:18](=[N:19][OH:20])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:6]2=[N:7][C:8]=1[C:9]([NH2:11])=[O:10])#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].O>CN(C=O)C>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][O:20][N:19]=[C:18]1[C:5]2[C:6](=[N:7][C:8]([C:9](=[O:10])[NH2:11])=[C:3]([C:1]#[N:2])[N:4]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]1=2)[CH3:33]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 178510554HCID 178510554, Verbindung

Produkt 1

HCID 76577927HCID 76577927, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a suspension of 33 (300 mg, 1.1 mmol) and Cs2CO3 (405 mg, 1.2 mmol) in DMF (15 ml), ethyl bromoacetate (0.14 ml, 1.26 mmol) was added dropwise and the mixture was stirred at 70° C. for 24 h. The suspension was cooled at room temperature, H2O (30 ml) was added and the mixture was extracted with CH2Cl2 (70 ml). The organic phase was dried over Na2SO4 and the volatile solvent was evaporated under reduced pressure. A 1:1 mixture of n-hexane/iPr2O was added and after 2 h the obtained solid was collected by filtration. The crude was purified by flash chromatography (CH2Cl2/MeOH 85:15) affording 37 (85 mg, 22%) as green-brown solid. 1H NMR (300 MHz, DMSO d6): δ 8.78 (bs, 1H), 8.73 (bs, 1H), 8.00 (dd, 1H), 7.82 (m, 2H), 7.67 (ddd, 1H), 4.87 (s, 2H), 4.19 (q, 2H), 1.25 (t, 3H). ESI+MS: calcd for C17H13N5O4: 351.32; found: 352.1 (MH+).

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureThe suspension was cooled at room temperature
  3. extractionthe mixture was extracted with CH2Cl2 (70 ml)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe volatile solvent was evaporated under reduced pressure
  6. additionA 1:1 mixture of n-hexane/iPr2O
  7. additionwas added and after 2 h the obtained solid
  8. filtrationwas collected by filtration
  9. customThe crude was purified by flash chromatography (CH2Cl2/MeOH 85:15)

Quellen und Nachweise

ORD-Eintrag
ord-1d67041e9bd3435b97d7f727522334a8
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08648076B2

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