1-(2-Methoxyethyl)piperazine → 2-{6-[4-(2-Methoxyethyl)piperazin-1-yl]pyrimidin-4-yl}-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one dihydrochloride

HRID 37903

Reaktionsgleichung

Reaktionsgleichung von HRID 37903
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12](=[O:13])[C:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][NH:9]2)[CH:3]=1.[CH3:20][O:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C1COCC1>[ClH:1].[ClH:1].[CH3:20][O:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([N:8]3[C:12](=[O:13])[C:11]([C:14]4[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=4)=[CH:10][NH:9]3)[CH:3]=2)[CH2:26][CH2:25]1

Komponenten

4

Edukt 2

HCID 27346381-(2-Methoxyethyl)piperazineHCID 866723282-(6-Chloropyrimidin-4-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

Produkt 1

HCID 688050852-{6-[4-(2-Methoxyethyl)piperazin-1-yl]pyrimidin-4-yl}-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

100 mg (0.4 mmol) of the compound from Example 23 and 113 mg (0.7 mmol) of N-(methoxy-ethyl)piperazine are initially charged in 3 ml of THF. The reaction mixture is reacted in a single-mode microwave oven (Emrys Optimizer) at 120° C. for 20 min. The cooled reaction solution is then concentrated on a rotary evaporator, and the residue is chromatographed by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid). 1 ml of a 4 N solution of hydrogen chloride in dioxane is added to the resulting formate salt of the target compound, and the mixture is stirred at RT for 30 min. The suspension is then concentrated under reduced pressure, and the residue is dried.

Aufarbeitung

  1. customThe reaction mixture is reacted in a single-mode microwave oven (Emrys Optimizer) at 120° C. for 20 min
  2. customThe cooled reaction solution
  3. concentrationis then concentrated on a rotary evaporator
  4. customthe residue is chromatographed by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)
  5. addition1 ml of a 4 N solution of hydrogen chloride in dioxane is added to the resulting formate salt of the target compound
  6. concentrationThe suspension is then concentrated under reduced pressure
  7. customthe residue is dried

Quellen und Nachweise

ORD-Eintrag
ord-05c5bf2623c84748a380e226ad03f216
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524699B2

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