Dimethylpiperazine → HCID 178489806, Verbindung

HRID 16827

Reaktionsgleichung

Reaktionsgleichung von HRID 16827
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[NH:12][N:13]=[C:14]([CH2:16][CH2:17][C:18]3[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[CH:19]=3)[CH:15]=2)=[O:9])=[N:6][CH:7]=1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH:30]1[CH3:35]>CS(C)=O>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][C:14]2[CH:15]=[C:11]([NH:10][C:8]([C:5]3[CH:4]=[N:3][C:2]([N:32]4[CH2:33][CH2:34][N:29]([CH3:28])[CH:30]([CH3:35])[CH2:31]4)=[CH:7][N:6]=3)=[O:9])[NH:12][N:13]=2)[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=1

Komponenten

4

Edukt 2

HCID 198037DimethylpiperazineHCID 178489782HCID 178489782, Verbindung

Produkt 1

HCID 178489806HCID 178489806, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

5-Chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide (388 mg, 1.00 mmol) was added in one portion to 1,2-dimethyl-piperazine (228 mg, 2.00 mmol) in anhydrous dimethylsulfoxide (2.00 ml) at 25° C. The resulting solution was stirred at ambient temperature for 2 h. The residue was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH to afford impure material. The concentrated eluent was purified by silica column chromatography, eluting with a gradient of 0 to 10% 7M NH3/MeOH in DCM. Pure fractions were evaporated to dryness to afford the title compound (375 mg, 81%) as a yellow solid.

Aufarbeitung

  1. customThe residue was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customto afford impure material
  4. customThe concentrated eluent was purified by silica column chromatography
  5. washeluting with a gradient of 0 to 10% 7M NH3/MeOH in DCM
  6. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-81846023ad3a4bcdb950d4d112da7393
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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