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Acetonitrile → 1-[4-[2-[4-(6-Chloro-1H-indazol-3-yl)1-piperazinyl]ethoxy]-3-methoxyphenyl]-ethanone

HRID 1080059
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1080059
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][C:28]=1[O:36][CH3:37].C(#N)C>O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:12][CH2:13][N:14]([CH2:24][CH2:25][O:26][C:27]4[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][C:28]=4[O:36][CH3:37])[CH2:15][CH2:16]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 144071701-[4-(2-Chloroethoxy)-3-methoxyphenyl]ethanoneHCID 148234706-chloro-3-(1-piperazinyl)-1H-indazole

Produkt 1

HCID 219600041-[4-[2-[4-(6-Chloro-1H-indazol-3-yl)1-piperazinyl]ethoxy]-3-methoxyphenyl]-ethanoneAusbeute 41,9 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 6-chloro-[3-(1-piperazinyl)]-1H-indazole (2.1 g, 8.9 mmol), K2CO3 (1.5 g, 10.7 mmol), KI (100 mg), 1-[4-(2-chloroethoxy)-3-methoxyphenyl]ethanone (2.2 g, 9.8 mml) and acetonitrile (70 ml) was stirred at reflux for 48 hours under N2The cooled reaction was poured into water and the aqueous mixture was extracted with ethyl acetate. The organic extract was washed with water, dried with MgSO4 and concentrated to yield 6.0 of a light yellow oil. The oil was purified by preparative HPLC (Waters Associates prep LC/System 500, employing 2 silica gel columns and 5.5% methanol/methylene chloride as eluent). Concentration of later fractions provided 1.6 g of an off-white solid. This was combined with an additional sample (3.4 g total) and two consecutive recrystallizations from ethanol yielded 2.1 g (23%) of 1-[4-[2-[4-(6-chloro-1H-indazol-3-yl)-1-piperazinyl]ethoxy]-3-methoxyphenphenyl]ethanone as an off-white solid, m.p.=154°-156° C.

Aufarbeitung

  1. temperatureat reflux for 48 hours under N2The cooled reaction
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customto yield 6.0 of a light yellow oil
  8. customThe oil was purified by preparative HPLC (Waters Associates prep LC/System 500, employing 2 silica gel columns and 5.5% methanol/methylene chloride as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-ab500878e24e44099429f3c78064e9ff
Quelldatensatz
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05580887

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