Dimethylformamide → 4-[1-(4-methoxyphenyl)-1H-indazol-3-yl]-1-piperazine carboxamide

HRID 359037

Reaktionsgleichung

Reaktionsgleichung von HRID 359037
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[N:11]2)=[CH:6][CH:5]=1.[N+]([NH:28][C:29](N)=[O:30])([O-])=O.CN(C)C=O>O>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([N:19]3[CH2:24][CH2:23][N:22]([C:29]([NH2:28])=[O:30])[CH2:21][CH2:20]3)=[N:11]2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 62372NitroureaHCID 198870561-(4-methoxyphenyl)-3-(1-piperazinyl)-1H-indazole hydrochloride

Produkt 1

HCID 151171164-[1-(4-methoxyphenyl)-1H-indazol-3-yl]-1-piperazine carboxamideAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 1-(4-methoxyphenyl)-3-(1-piperazinyl)-1H-indazole hydrochloride (5.0 g, 0.01 mol), nitrourea (4.0 g, 0.04 mol) and dimethylformamide (200 ml) was warmed on a steam bath for 2 hours. The reaction mixture was poured into H2O and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate was dried with MgSO4 and concentrated to 5.3 g of an oil. Crystallization was achieved with toluene affording 3.3 g (65%) of a powder. The powder was recrystallized again from toluene to afford 3.0 g of 4-[1-(4-methoxyphenyl)-1H-indazol-3-yl]-1-piperazine carboxamide, m.p. 155°-157° C.

Aufarbeitung

  1. extractionthe aqueous mixture was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate was dried with MgSO4
  3. concentrationconcentrated to 5.3 g of an oil
  4. customCrystallization
  5. customThe powder was recrystallized again from toluene

Quellen und Nachweise

ORD-Eintrag
ord-7aee8f4086a642e3b79ffdea564f49a0
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04999356

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