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1,2-Diaminocyclohexane → 1-(3-chloro-4-fluorophenyl)-6-[4-(2-oxo-1-piperidinyl)phenyl]-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one

HRID 890514
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 890514
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3[C:14](=[O:25])[N:15]([C:18]4[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:26]([F:29])([F:28])[F:27])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[C:30]1(=[O:36])[NH:35][CH2:34][CH2:33][CH2:32][CH2:31]1.NC1CCCCC1N.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.C(OC(=O)C)C.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3[C:14](=[O:25])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([N:35]5[CH2:34][CH2:33][CH2:32][CH2:31][C:30]5=[O:36])=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:26]([F:29])([F:28])[F:27])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 46101,2-DiaminocyclohexaneHCID 126652-PiperidoneHCID 62657Potassium Phosphate, TribasicHCID 222404461-(3-chloro-4-fluorophenyl)-6-[4-iodophenyl]-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one

Produkt 1

HCID 102075641-(3-chloro-4-fluorophenyl)-6-[4-(2-oxo-1-piperidinyl)phenyl]-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one
Ausbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Part B. 1-(3-chloro-4-fluorophenyl)-6-[4-iodophenyl]-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridine-7-one (0.54 g, 1.0 mmol), δ-valerolactam (0.12 g, 1.2 mmol), 1,2-diaminocyclohexane (11.4 mg, 0.1 mmol), K3PO4 (0.42 g, 2 mmol) and CuI (2 mg, 0.01 mmol) were added to 5 mL of 1,4-dioxane. The mixture was degassed under argon and stirred at 110° C. under N2 for 48 h. The mixture was then cooled to rt. The dioxane was removed. The residue was dissolved in EtOAc (100 mL), washed with HCl (1N, 30 mL), water (50 mL×2), and brine (50 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified via flash chromatography on silica gel using 1:2 hexane:ethylacetate to give the desired product (0.41 g, 80% yield). LRMS (ES+): 507.1 (M+H)+. 1H NMR (CDCl3) δ 7.68–7.65 (m, 1H), 7.50–7.45 (m, 1H), 7.36–7.16 (m, 5H), 4.16 (t, 2H), 3.64–3.62 (m, 2H), 3.47 (br, 3H), 3.17 (t, 2H), 2.62 (t, 2H), 1.98–1.96 (m, 3H).

Aufarbeitung

  1. customThe mixture was degassed under argon
  2. temperatureThe mixture was then cooled to rt
  3. customThe dioxane was removed
  4. dissolutionThe residue was dissolved in EtOAc (100 mL)
  5. washwashed with HCl (1N, 30 mL), water (50 mL×2), and brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified via flash chromatography on silica gel using 1:2 hexane

Quellen und Nachweise

ORD-Eintrag
ord-da911549baed4470bcf02e03af5bbd35
Quelldatensatz
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06995172B2

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