1,2-Diaminocyclohexane → 1-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-one

HRID 80241

Reaktionsgleichung

Reaktionsgleichung von HRID 80241
[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.Br[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[Cl:23].C1(N)CCCCC1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(Cl)(Cl)Cl.[Cu](I)I.CO.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[Cl:23])[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Komponenten

9

Edukt 4

HCID 46101,2-DiaminocyclohexaneHCID 62657Potassium Phosphate, TribasicHCID 8176963-Bromo-4-chloropyridineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Produkt 1

HCID 596362211-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717Copper iodideKatalysatorHCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions and work up as described in Example 1, step-3,1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 800 mg, 3.653 mmol) was refluxed with 3-bromo-4-chloro-pyridine (879 mg, 4.566 mmol), copper iodide (70 mg, 0.365 mmol), cyclohexane-1,2-diamine (125 mg, 1.0958 mmol), potassium phosphate (2.32 g, 10.958 mmol) and 1,4-Dioxane (50 mL) at 110° C. for 12 hours to afford the crude product. The reaction was monitored by TLC (10% MeOH in chloroform). Purification by column chromatography on silica gel (1.5% methanol in chloroform) afforded 715 mg of the product (60% yield).

Aufarbeitung

  1. customthe same reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1.5% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-800efc2c8ea84b14949952a612a07b65
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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