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Sodium hydride → 6,7-Dichloro-2,3-dimethoxy-5-{4-[3-(4-morpholinyl)propyl]pyrazol-1-ylmethyl}quinoxaline

HRID 1957112
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Reaktionsgleichung

Reaktionsgleichung von HRID 1957112
Cl.Cl.[N:3]1([CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[N:14][NH:15][CH:16]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[H-].[Na+].Br[CH2:20][C:21]1[C:30]([Cl:31])=[C:29]([Cl:32])[CH:28]=[C:27]2[C:22]=1[N:23]=[C:24]([O:35][CH3:36])[C:25]([O:33][CH3:34])=[N:26]2.[Cl-].[NH4+]>O>[Cl:31][C:30]1[C:21]([CH2:20][N:15]2[CH:16]=[C:12]([CH2:11][CH2:10][CH2:9][N:3]3[CH2:8][CH2:7][O:6][CH2:5][CH2:4]3)[CH:13]=[N:14]2)=[C:22]2[C:27](=[CH:28][C:29]=1[Cl:32])[N:26]=[C:25]([O:33][CH3:34])[C:24]([O:35][CH3:36])=[N:23]2
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Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 105459165-Bromomethyl-6,7-dichloro-2,3-dimethoxyquinoxalineHCID 190689104-[3-(4-Morpholinyl)propyl]pyrazole dihydrochloride

Produkt 1

HCID 190688746,7-Dichloro-2,3-dimethoxy-5-{4-[3-(4-morpholinyl)propyl]pyrazol-1-ylmethyl}quinoxalineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

4-[3-(4-Morpholinyl)propyl]pyrazole dihydrochloride (268 mg, 1 mmol) was added to a stirred suspension of sodium hydride (120 mg, 80% oil dispersion, 4 mmol) at 0° C. under nitrogen. After 30 minutes, the mixture was cooled to -40° C. and 5-bromomethyl-6,7-dichloro-2,3-dimethoxyquinoxaline (Preparation 1, 235 mg, 0.67 mmol) was added. The mixture was allowed to warm to -20° C. over 1 hour and saturated aqueous ammonium chloride (20 mL) was added. The mixure was diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The extracts were washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with dichloromethane, then ethyl acetate then finally ethyl acetate:methanol:triethylamine (100:3:1) to give 6,7-dichloro-2,3-dimethoxy-5-{4-[3-(4-morpholinyl)propyl]pyrazol-1-ylmethyl}quinoxaline (278 mg, 89%) as a colourless gum.

Aufarbeitung

  1. temperatureto warm to -20° C. over 1 hour
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-42b4e540b7a34c82a29c56ee14be9539
Quelldatensatz
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05783572

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