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Diethyl Ether → HCID 178508793, Verbindung

HRID 2365500
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2365500
[NH2:1][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:9][NH:8]/[C:7](=[N:10]\[C:11]([C:13]2[C:18]([NH2:19])=[N:17][C:16]([NH2:20])=[C:15]([Cl:21])[N:14]=2)=[O:12])/[NH:6]1.[C:22]([N:29]1[CH:33]=[CH:32]N=C1)(N1C=CN=C1)=[O:23].C(N)[C:35]1[CH:40]=[CH:39]C=[CH:37][CH:36]=1.C(OCC)C>CN(C=O)C.CO>[CH2:33]([NH:29][C:22](=[O:23])[NH:1][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:9][NH:8]/[C:7](=[N:10]\[C:11]([C:13]2[C:18]([NH2:19])=[N:17][C:16]([NH2:20])=[C:15]([Cl:21])[N:14]=2)=[O:12])/[NH:6]1)[C:32]1[CH:39]=[CH:40][CH:35]=[CH:36][CH:37]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 7504Benzylamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 178511031HCID 178511031, Verbindung

Produkt 1

HCID 178508793HCID 178508793, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid [(S)-4-(3-amino-propyl)-imidazolidin-(2E)-ylidene]-amide (Ex. 31) (0.040 g, 0.128 mmol) in DMF (2 ml) is added 1,1′-carbonyldiimidazole (0.023 g, 0.141 mmol) and the reaction mixture is stirred for 1 hour at room temperature. Benzylamine (0.014 ml, 0.128 mmol) is added and additional benzylamine (0.014 ml, 0.128 mmol) is added at hourly intervals for a total of 3 hours. Purification is by diluting the reaction with 2N NaOH (30 ml) and extracting the product into EtOAc (40 ml). The organic phase is washed with 2N NaOH (30 ml), dried over MgSO4 and the solvent evaporated in vacuo to yield a yellow oil. The oil is dissolved in methanol (0.75 ml) and diethyl ether (5 ml) added to triturate a yellow solid. This solid is filtered off and the filtrate formed a further precipitate. This yellow solid is collected by filtration and rinsed with diethyl ether to give the title compound; [M+H]+ 446.1

Aufarbeitung

  1. customPurification
  2. additionby diluting
  3. customthe reaction with 2N NaOH (30 ml)
  4. extractionextracting the product into EtOAc (40 ml)
  5. washThe organic phase is washed with 2N NaOH (30 ml)
  6. dry with materialdried over MgSO4
  7. customthe solvent evaporated in vacuo
  8. customto yield a yellow oil
  9. customto triturate a yellow solid
  10. filtrationThis solid is filtered off
  11. customthe filtrate formed a further precipitate
  12. filtrationThis yellow solid is collected by filtration
  13. washrinsed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-fe705dd5996b40bf8822791ca2dd6998
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08697687B2

Notizen zur Reaktion

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