Potassium sodium tartarate → N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]-5-(3,4-dimethylpiperazin-1-yl)thiophene-2-carboxamide

HRID 1092067

Reaktionsgleichung

Reaktionsgleichung von HRID 1092067
C[Al](C)C.[CH3:5][CH:6]1[N:11]([CH3:12])[CH2:10][CH2:9][N:8]([C:13]2[S:17][C:16]([C:18]([O:20]CC)=O)=[CH:15][CH:14]=2)[CH2:7]1.Cl.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:34][O:35][C:36]2[CH:37]=[C:38]([NH2:41])[NH:39][N:40]=2)[CH:29]=[C:30]([O:32][CH3:33])[CH:31]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH3:33][O:32][C:30]1[CH:29]=[C:28]([CH2:34][O:35][C:36]2[CH:37]=[C:38]([NH:41][C:18]([C:16]3[S:17][C:13]([N:8]4[CH2:9][CH2:10][N:11]([CH3:12])[CH:6]([CH3:5])[CH2:7]4)=[CH:14][CH:15]=3)=[O:20])[NH:39][N:40]=2)[CH:27]=[C:26]([O:25][CH3:24])[CH:31]=1

Komponenten

8

Edukt 4

HCID 9855836Potassium sodium tartarateHCID 16682925TrimethylaluminumHCID 574403805-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine hydrochlorideHCID 57440412Ethyl 5-(3,4-dimethylpiperazin-1-yl)thiophene-2-carboxylate

Produkt 1

HCID 66589605N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]-5-(3,4-dimethylpiperazin-1-yl)thiophene-2-carboxamideAusbeute 7,63 %

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-(3,4-dimethylpiperazin-1-yl)thiophene-2-carboxylate (0.268 g, 1 mmol) and 5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine hydrochloride (0.286 g, 1.00 mmol) in toluene (7.14 ml) at 80° C. under nitrogen for 4 h and then at 70° C. for 18 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 gum. The crude product was purified by preparative LCMS, 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 (0.036 g, 7.63%) as a white solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a4b8be62c5b449d39fac005d0c5d42be
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129391B2

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