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Hydrochloric Acid → HCID 178462658, Verbindung

HRID 1092184
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1092184
C[Al](C)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]([NH2:22])[NH:20][N:21]=2)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1.[CH2:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:40]=[CH:39][C:34]([C:35](OC)=[O:36])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)[CH3:24].Cl>C1(C)C=CC=CC=1.CO>[CH3:14][O:13][C:11]1[CH:10]=[C:9]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]([NH:22][C:35](=[O:36])[C:34]3[CH:33]=[CH:32][C:31]([N:28]4[CH2:27][CH2:26][N:25]([CH2:23][CH3:24])[CH2:30][CH2:29]4)=[CH:40][CH:39]=3)[NH:20][N:21]=2)[CH:8]=[C:7]([O:6][CH3:5])[CH:12]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 16682925TrimethylaluminumHCID 57781922Methyl 4-(4-ethylpiperazin-1-yl)benzoateHCID 178489815HCID 178489815, Verbindung

Produkt 1

HCID 178462658HCID 178462658, VerbindungAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Trimethylaluminium (2M in toluene, 1.51 mL, 3.02 mmol) was added dropwise to 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (299 mg, 1.21 mmol) and methyl 4-(4-ethylpiperazin-1-yl)benzoate (300 mg, 1.21 mmol) in toluene (6.0 mL) at 25° C. The resulting suspension was stirred at 60° C. for 24 h under nitrogen. The reaction mixture was added to methanol (100 mL) and was treated with HCl (2N aqueous solution, until the pH was 7 or lower). The crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford impure product. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 5% 7M NH3/MeOH in DCM. Pure fractions were evaporated to dryness to afford the title compound (288 mg, 51%) as a cream solid.

Aufarbeitung

  1. customThe crude product was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customwere evaporated to dryness
  4. customto afford impure product
  5. customThe crude product was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 5% 7M NH3/MeOH in DCM
  7. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-de69bf68b99246a0baaaff1f2a5cb28d
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08129391B2

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