Hydrochloric Acid → HCID 178485325, Verbindung

HRID 1911482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911482
C[Al](C)C.[NH2:5][C:6]1[NH:10][N:9]=[C:8]([CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([NH:18][CH3:19])=[O:17])[CH:7]=1.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:39]=[CH:38][C:33]([C:34](OC)=[O:35])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1.Cl>C1(C)C=CC=CC=1.CO>[CH3:19][NH:18][C:16]([C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][C:8]2[CH:7]=[C:6]([NH:5][C:34](=[O:35])[C:33]3[CH:32]=[CH:31][C:30]([N:27]4[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]4)=[CH:39][CH:38]=3)[NH:10][N:9]=2)[CH:22]=[CH:21][CH:20]=1)=[O:17]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1472668Methyl 4-(4-methylpiperazin-1-yl)benzoateHCID 16682925TrimethylaluminumHCID 178485326HCID 178485326, Verbindung

Produkt 1

HCID 178485325HCID 178485325, VerbindungAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A 2M solution of trimethylaluminium (0.936 mL, 1.87 mmol) in toluene, was added drop-wise to a stirred suspension of 3-(2-(5-amino-1H-pyrazol-3-yl)ethyl)-N-methylbenzamide (0.183 g, 0.75 mmol) and methyl 4-(4-methylpiperazin-1-yl)benzoate (0.176 g, 0.75 mmol) in toluene (5 mL) at room temperature. The solution was then stirred at 60° C. for 18 h. The reaction mixture was cooled, poured into methanol (5 ml) and acidified with 2N HCl (15 ml). 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 pure fractions were evaporated to dryness to afford an oil. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (0.109 g, 32.6%) as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customThe crude product was purified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. customwere evaporated to dryness
  5. customto afford an oil
  6. customThe crude product was purified by preparative HPLC
  7. additionFractions containing the desired compound
  8. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b8402f3b377a49169340d5f4da544874
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604022B2

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