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Sodium Methoxide → 2-((2-Methoxypyridin-4-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41569
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 41569
Br[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C:11]3([CH2:19][CH2:18][N:17]([C:20]4[CH:29]=[N:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)[CH2:16][CH2:15]3)[C:10]2=[O:30])[CH:5]=[CH:4][N:3]=1.[CH3:31][O-:32].[Na+]>CO>[CH3:31][O:32][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C:11]3([CH2:19][CH2:18][N:17]([C:20]4[CH:29]=[N:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)[CH2:16][CH2:15]3)[C:10]2=[O:30])[CH:5]=[CH:4][N:3]=1
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Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 718111802-((2-Bromopyridin-4-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one2×

Produkt 1

HCID 532596382-((2-Methoxypyridin-4-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-oneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The title compound was synthesized from 2-((2-bromopyridin-4-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (prepared according to method D) as follows: A stirred solution of 2-((2-bromopyridin-4-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (synthesized according to method D) (70 mg, 0.15 mmol) and NaOMe (40.6 mg, 0.75 mmol) in MeOH (2 mL) was heated at 100° C. for 18 h. The reaction mixture was cooled to rt and the solvent was evaporated under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was washed with hexane to yield the title compound (55 mg, 68%). [1H NMR (300 MHz, CDCl3) ♀ ppm 8.60 (s, 1H), 8.12 (d, 1H), 7.85 (d, 1H), 7.68 (d, 1H), 7.56 (t, 1H), 7.38 (t, 1H), 6.75 (d, 1H), 6.55 (s, 1H), 4.56 (s, 2H), 4.31-4.13 (m, 2H), 3.92 (s, 3H), 3.70-3.55 (m, 2H), 3.25 (br s, 2H), 2.40-2.25 (m, 2H), 1.98-1.80 (m, 4H), 1.78-1.50 (m, 2H); LCMS RtF=1.30 min, [M+H]+=418.0].

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washThe crude product was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-ffbe8285b284460d9eb7593ce15b4521
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08530648B2

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