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Diisopropylethylamine → 6-chloro-4'-(3-chlorophenyl)-2'-(5-fluoro-2-methylphenyl)-1'-(3-morpholin-4-yl-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728015
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1728015
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:36])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[N:12]([CH2:24][CH2:25][CH2:26]Cl)[CH:11]3[C:28]3[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=3[CH3:35])[C:5]2=[CH:4][CH:3]=1.[CH3:37][O:38][CH:39]([Si](C)(C)C)[CH3:40].C[CH2:46][N:47](C(C)C)C(C)C>N1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:36])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[N:12]([CH2:24][CH2:25][CH2:26][N:47]4[CH2:40][CH2:39][O:38][CH2:37][CH2:46]4)[CH:11]3[C:28]3[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=3[CH3:35])[C:5]2=[CH:4][CH:3]=1
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Komponenten

4

Edukt 2

HCID 81531DiisopropylethylamineHCID 775807906-Chloro-4'-(3-chlorophenyl)-1'-(3-chloro-propyl)-2'-(5-fluoro-2-methylphenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Produkt 1

HCID 1317273286-chloro-4'-(3-chlorophenyl)-2'-(5-fluoro-2-methylphenyl)-1'-(3-morpholin-4-yl-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneAusbeute 37,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8083
Morpholine
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

The mixture of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-2,3-dihydro-1′-(3-chloro-propyl)-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (0.24 g, 0.36 mmol) prepared in example 60a and morpholine (10 mL) was heated at 120° C. for 1 h. The mixture was concentrated to dryness. The resulting residue was added dichloromethane (20 mL) and then trifluoroacetic acid (20 mL). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was separated and concentrated. The residue was redissolved in methanol (10 mL). To the resulting solution was added N,N′-diisopropylethylamine (2 mL, 11.0 mmol) and the crude was heated at 100° C. for 1 h. The reaction mixture was concentrated and the residue was purified by chromatography (MeOH:EtOAc=1:9) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-1′-(3-morpholin-4-yl-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.08 g, 37.9%).

Aufarbeitung

  1. concentrationThe mixture was concentrated to dryness
  2. additionThe resulting residue was added dichloromethane (20 mL)
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was partitioned between ethyl acetate and saturated NaHCO3 solution
  5. customThe organic layer was separated
  6. concentrationconcentrated
  7. dissolutionThe residue was redissolved in methanol (10 mL)
  8. temperaturethe crude was heated at 100° C. for 1 h
  9. concentrationThe reaction mixture was concentrated
  10. customthe residue was purified by chromatography (MeOH:EtOAc=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-478fa437f22e441ab4b0793265cdd27e
Quelldatensatz
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07495007B2

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