Iodine → HCID 57444149, Verbindung

HRID 44627

Reaktionsgleichung

Reaktionsgleichung von HRID 44627
N[C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([NH:18][C@@H:19]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.[I-:33].[Cs+].II.N(OCCC(C)C)=O>C(COC)OC.[Cu](I)I>[I:33][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([NH:18][C@@H:19]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:20][N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1

Komponenten

7

Edukt 4

HCID 807IodineHCID 8053Isoamyl NitriteHCID 24601Cesium iodideHCID 574441508-amino-1-methyl-N-[(1S)-2-morpholin-4-yl-1-phenylethyl]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Produkt 1

HCID 57444149HCID 57444149, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a well stirred and warm suspension of 8-amino-1-methyl-N-[(1S)-2-morpholin-4-yl-1-phenylethyl]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (3 g, 6.92 mmol) in dimethoxyethane (240 mL), maintained in an inert atmosphere of argon, cesium iodide (2.16 g, 8.3 mmol), bisublimated iodine (870 mg, 3.46 mmol), copper iodide (460 mg, 2.42 mmol) and isopentyl nitrite (1.71 mL, 1.5 g, 12.46 mmol) were added, in sequence. The reaction mixture was stirred vigorously at 65-70° C. for 18 hours. After cooling in an ice-water bath, the solid was filtered off and the filtrate was diluted with dichloromethane (100 mL), washed with 30% ammonium hydroxide (50 mL), sodium thiosulphate (100 mL), brine and dried over anhydrous Na2SO4. The crude was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 95:59) and 1.48 g of the title compound was isolated (40% yield).

Aufarbeitung

  1. temperaturewarm
  2. additionwere added, in sequence
  3. stirringThe reaction mixture was stirred vigorously at 65-70° C. for 18 hours
  4. temperatureAfter cooling in an ice-water bath
  5. filtrationthe solid was filtered off
  6. additionthe filtrate was diluted with dichloromethane (100 mL)
  7. washwashed with 30% ammonium hydroxide (50 mL), sodium thiosulphate (100 mL), brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe crude was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 95:59)

Quellen und Nachweise

ORD-Eintrag
ord-b27aceb55e484bbc8f9a5441de48ba65
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541429B2

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