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Sodium borohydride → 6-Tert-butyl-8-fluoro-2-[3-(hydroxymethyl)-4-[1-methyl-5-[(5-methylisoxazol-3-yl)amino]-6-oxo-3-pyridyl]-2-pyridyl]phthalazin-1-one

HRID 1185239
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1185239
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[N:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:36]=[C:35]([CH3:37])[O:34][N:33]=4)[C:28](=[O:38])[N:27]([CH3:39])[CH:26]=3)[C:18]=1[CH:19]=[O:20])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[C:18]([CH2:19][OH:20])=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:36]=[C:35]([CH3:37])[O:34][N:33]=4)[C:28](=[O:38])[N:27]([CH3:39])[CH:26]=3)[CH:22]=[CH:23][N:24]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]
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Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 866840882-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-5-(5-methylisoxazol-3-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)nicotinaldehyde

Produkt 1

HCID 866839796-Tert-butyl-8-fluoro-2-[3-(hydroxymethyl)-4-[1-methyl-5-[(5-methylisoxazol-3-yl)amino]-6-oxo-3-pyridyl]-2-pyridyl]phthalazin-1-oneAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

To a solution of 161b (300 mg, 0.57 mmol) in methanol (10 mL) was added NaBH4 (108 mg, 2.85 mmol) at room temperature. After the reaction was stirred for 6 h, LCMS indicated the reaction was complete. It was then quenched with water (10 mL) and concentrated under reduced pressure. The resulting residue was extracted with dichloromethane (3×20 mL). The combined organic layer was washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue solid was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (1:20 to 100% ethyl acetate) to afford 161c (164 mg, 54%) as a white solid. MS-ESI: [M+H]+ 530.8

Aufarbeitung

  1. customIt was then quenched with water (10 mL)
  2. concentrationconcentrated under reduced pressure
  3. extractionThe resulting residue was extracted with dichloromethane (3×20 mL)
  4. washThe combined organic layer was washed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue solid was purified by silica-gel column chromatography
  9. washeluting with petroleum ether/ethyl acetate (1:20 to 100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7e1b81363173409c8d88bd6cfb746280
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08669251B2

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