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1,2-Diaminocyclohexane → (S)-4-(1H-benzo[d]imidazol-6-yl)-5-(4-propoxyphenyl)morpholin-3-one

HRID 452096
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 452096
F[C:2](F)(F)C([O-])=O.[CH2:8]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]2[NH:23][C:22](=[O:24])[CH2:21][O:20][CH2:19]2)=[CH:14][CH:13]=1)[CH2:9][CH3:10].I[C:26]1[CH:27]=[C:28]([NH2:33])[C:29]([NH2:32])=[CH:30][CH:31]=1.[F-].[Cs+].C1(N)CCCCC1N>[Cu]I>[NH:33]1[C:28]2[CH:27]=[C:26]([N:23]3[C@@H:18]([C:15]4[CH:14]=[CH:13][C:12]([O:11][CH2:8][CH2:9][CH3:10])=[CH:17][CH:16]=4)[CH2:19][O:20][CH2:21][C:22]3=[O:24])[CH:31]=[CH:30][C:29]=2[N:32]=[CH:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 46101,2-DiaminocyclohexaneHCID 25953Cesium fluorideHCID 84468TrifluoroacetateHCID 112070494-Iodobenzene-1,2-diamineHCID 58229161(S)-5-(4-propoxyphenyl)morpholin-3-one

Produkt 1

HCID 51030217(S)-4-(1H-benzo[d]imidazol-6-yl)-5-(4-propoxyphenyl)morpholin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

The final product was synthesized as trifluoroacetate salt starting from (S)-5-(4-propoxyphenyl)morpholin-3-one (0.044 g, 0.19 mmol), 4-iodobenzene-1,2-diamine (0.044 g, 0.19 mmol), copper(I) iodide (0.004 g, 0.019 mmol), cesium fluoride (0.058 g, 0.38 mmol), cyclohexane-1,2-diamine (0.0025 mL, 0.019 mmol). The solids were given together in a reaction flask and the flask was purged with argon. A solution of cyclohexane-1,2-diamine in 2 mL dioxane was added to the flask. The reaction was stirred at 95° C. for 4 days, before the reaction was cooled down to 45° C. and filtered through a pad of celite. The pad was washed with warm dichloromethane and the solution was concentrated under reduced pressure. The intermediate product was purified via FPLC using a chloroform-methanol gradient (0→10%) Yield: 0.01 g (15%); MS m/z 342.2 (M+H)+

Aufarbeitung

  1. customThe solids were given together in a reaction flask
  2. customthe flask was purged with argon
  3. additionA solution of cyclohexane-1,2-diamine in 2 mL dioxane was added to the flask
  4. temperaturewas cooled down to 45° C.
  5. filtrationfiltered through a pad of celite
  6. washThe pad was washed with warm dichloromethane
  7. concentrationthe solution was concentrated under reduced pressure
  8. customThe intermediate product was purified via FPLC

Quellen und Nachweise

ORD-Eintrag
ord-0fde2d7b2c8249a391872e62a29b193e
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08486940B2

Notizen zur Reaktion

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