1,2-Diaminocyclohexane, trans- → N-[3-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-pyridin-4-yl]-acetamide

HRID 80195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 80195
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.I[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[NH:23][C:24](=[O:26])[CH3:25].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][C:22]=4[NH:23][C:24](=[O:26])[CH3:25])[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Komponenten

7

Edukt 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 53342836N-(3-Iodo-4-pyridinyl)acetamideHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Produkt 1

HCID 59636268N-[3-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-pyridin-4-yl]-acetamideAusbeute 23,36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions as in Example 14, 1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 200 mg, 0.912 mmol) was reacted with N-(3-iodo-pyridin-4-yl)-acetamide (262 mg, 1.003 mmol), 1,4-dioxane (10 mL), copper iodide (17.3 mg, 0.09 mmol), trans-1,2-diamino cyclohexane (31.4 mg, 0.273 mmol) and potassium phosphate (581 mg, 2.73 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 75 mg of the product (23.36% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-498e4a0537384920904d41d0adbcac6c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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