Potassium sodium tartarate → HCID 178489773, Verbindung

HRID 16810

Reaktionsgleichung

Reaktionsgleichung von HRID 16810
C[Al](C)C.[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:16][C:15]([C:17]([O:19]CC)=O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:32][CH2:33][C:34]2[CH:35]=[C:36]([NH2:39])[NH:37][N:38]=2)[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH3:31][O:30][C:28]1[CH:27]=[C:26]([CH2:32][CH2:33][C:34]2[CH:35]=[C:36]([NH:39][C:17]([C:15]3[S:16][C:12]([N:9]4[CH2:8][CH2:7][N:6]([CH3:5])[CH2:11][CH2:10]4)=[CH:13][CH:14]=3)=[O:19])[NH:37][N:38]=2)[CH:25]=[C:24]([O:23][CH3:22])[CH:29]=1

Komponenten

8

Edukt 4

HCID 9855836Potassium sodium tartarateHCID 16682925TrimethylaluminumHCID 57440415Ethyl 5-(4-methylpiperazin-1-yl)thiophene-2-carboxylateHCID 178489815HCID 178489815, Verbindung

Produkt 1

HCID 178489773HCID 178489773, VerbindungAusbeute 33,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

2M Trimethylaluminium (1.250 ml, 2.50 mmol) in toluene, was added dropwise to a stirred solution of ethyl 5-(4-methylpiperazin-1-yl)thiophene-2-carboxylate (0.254 g, 1 mmol) and 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.247 g, 1.00 mmol) in toluene (7.14 ml) at 20° C. under nitrogen. The reaction mixture was stirred at ambient temperature for 16 h and then heated at 65° C. for 24 h. Ethyl acetate (5 mL) was added to the reaction mixture followed by a solution of potassium sodium tartrate (5 mL, 20% aqueous). More ethyl acetate (50 mL) and water (25 mL) was added and the mixture was filtered through celite. The filtrate was transferred to a separating funnel and the aqueous layer removed. The ethyl acetate layer was washed with saturated brine and then dried over magnesium sulphate. After filtration the solvent was evaporated to give the crude product as a yellow solid. 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 (0.154 g, 33.8%) as a white solid.

Aufarbeitung

  1. temperatureheated at 65° C. for 24 h
  2. filtrationthe mixture was filtered through celite
  3. customThe filtrate was transferred to a separating funnel
  4. customthe aqueous layer removed
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationAfter filtration the solvent
  8. customwas evaporated
  9. customto give the crude product as a yellow solid
  10. customThe crude product was purified by preparative HPLC
  11. additionFractions containing the desired compound
  12. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f81a7d3f374b487fb7e5042fe63efa6a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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