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Potassium Carbonate → 3-tert-Butyl-1'-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1'H-[1,4']bipyrazolyl-5-ylamine

HRID 630898
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 630898
I[C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:6]=1.[C:17]([C:21]1[CH:22]=[C:23]([NH2:26])[NH:24][N:25]=1)([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O.C1(C)C=CC=CC=1>[C:17]([C:21]1[CH:22]=[C:23]([NH2:26])[N:24]([C:2]2[CH:3]=[N:4][N:5]([CH2:7][CH2:8][CH2:9][O:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[CH:6]=2)[N:25]=1)([CH3:20])([CH3:19])[CH3:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 866871804-Iodo-1-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1H-pyrazoleHCID 178441179HCID 178441179, Verbindung

Produkt 1

HCID 866871823-tert-Butyl-1'-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1'H-[1,4']bipyrazolyl-5-ylamineAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a mixture of intermediate 113a (1.50 g, 4.46 mmol), 5-tert-butyl-2H-pyrazol-3-ylamine (620 mg, 4.46 mmol), copper (I) iodide (42 mg, 0.22 mmol) and K2CO3 (1.29 g, 9.37 mmol) was added a solution of toluene (4.6 mL), previously degassed by using a stream of argon. (R,R)-(−)-N,N′-Dimethyl-1,2-cyclohexanediamine (141 μL, 0.89 mmol) was then added and the reaction mixture was heated at 140° C. for 2.5 h under microwave irradiation. The crude reaction mixture was poured into water and extracted with EtOAc (×3). The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by FCC on silica, using a gradient of 0-100% EtOAc in cyclohexane, to give the title compound (1.14 g, 73%). LCMS (Method 4): Rt 2.34 min, m/z 348 [MH+].

Aufarbeitung

  1. custompreviously degassed
  2. customThe crude reaction mixture
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by FCC on silica

Quellen und Nachweise

ORD-Eintrag
ord-89ab88770c214d0f8c355d3ba8b6058f
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09315503B2

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