Potassium sodium tartarate → HCID 178489773, Verbindung

HRID 1092081

Reaktionsgleichung

Reaktionsgleichung von HRID 1092081
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 is 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. customat 20° C.
  2. temperatureheated at 65° C. for 24 h
  3. filtrationthe mixture was filtered through celite
  4. customThe filtrate was transferred to a separating funnel
  5. customthe aqueous layer removed
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried over magnesium sulphate
  8. filtrationAfter filtration the solvent
  9. customwas evaporated
  10. customto give the crude product as a yellow solid
  11. customThe crude product was purified by preparative HPLC
  12. additionFractions containing the desired compound
  13. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f53e76cf5cec4e36b020f5485d5de310
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129391B2

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