1,2-Diaminocyclohexane → 1-Benzothiazol-6-yl-3-pyridin-3-yl-4-trifluoromethyl-imidazolidin-2-one

HRID 80225

Reaktionsgleichung

Reaktionsgleichung von HRID 80225
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH:13]([C:15]([F:18])([F:17])[F:16])[NH:12][C:11]3=[O:19])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.C1(N)CCCCC1N.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][CH:13]([C:15]([F:17])([F:18])[F:16])[N:12]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[C:11]3=[O:19])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Komponenten

7

Edukt 4

HCID 46101,2-DiaminocyclohexaneHCID 122863-BromopyridineHCID 62657Potassium Phosphate, TribasicHCID 687879131-Benzothiazol-6-yl-4-trifluoromethyl-imidazolidin-2-one

Produkt 1

HCID 498726491-Benzothiazol-6-yl-3-pyridin-3-yl-4-trifluoromethyl-imidazolidin-2-oneAusbeute 23,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions and work up as described in example 1, step-3,1-Benzothiazol-6-yl-4-trifluoromethyl-imidazolidin-2-one (I-170b: 50 mg, 0.174 mmol) was refluxed with 3-Bromo-pyridine (33 mg, 0.209 mmol), copper iodide (3.3 mg, 0.0174 mmol), Cyclohexane-1,2-diamine (6 mg, 0.0522 mmol), potassium phosphate (110 mg, 0.522 mmol) and 1,4-Dioxane (2 mL) at 120° C. for 12 hours to afford the crude product. Purification by column chromatography on silica gel (2% methanol in chloroform) followed by n-pentane washing afforded 15 mg of the product (23.8% yield).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-10082d1ae133471d889e5801d44f73b2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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