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Ammonium Chloride → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-7-methyl-1H-[1,8]naphthyridin-4-one

HRID 226989
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 226989
[CH2:1]1[O:10][C:9]2[C:4](=[CH:5][C-:6]=[CH:7][CH:8]=2)[O:3][CH2:2]1.[Mg+2].[Br-].CON(C)[C:16]([C:18]1[C:27](=[O:28])[C:26]2[C:21](=[N:22][C:23]([CH3:29])=[CH:24][CH:25]=2)[N:20]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Br:37])[N:32]=2)[CH:19]=1)=[O:17].[Cl-].[NH4+]>C1COCC1>[Br:37][C:33]1[N:32]=[C:31]([CH2:30][N:20]2[C:21]3[C:26](=[CH:25][CH:24]=[C:23]([CH3:29])[N:22]=3)[C:27](=[O:28])[C:18]([C:16]([C:7]3[CH:6]=[CH:5][C:4]4[O:3][CH2:2][CH2:1][O:10][C:9]=4[CH:8]=3)=[O:17])=[CH:19]2)[CH:36]=[CH:35][CH:34]=1
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Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 15974803Magnesium bromide 2,3-dihydro-1,4-benzodioxin-6-ide (1/1/1)HCID 577545251-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide

Produkt 1

HCID 577546501-(6-Bromo-pyridin-2-ylmethyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-7-methyl-1H-[1,8]naphthyridin-4-oneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.896 mL of 3,4-(ethylenedioxy)phenylmagnesium bromide (0.448 mmol, 0.5M in THF) was added to 85 mg (0.204 mmol) of 1-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide dissolved in 1 mL of THF and the reaction was stirred at room temperature for 1 hour. Saturated ammonium chloride was added and the aqueous layer was extracted with dichloromethane (3×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography using 20-100% ethyl acetate in hexane and further purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 38.2 mg of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-7-methyl-1H-[1,8]naphthyridin-4-one as a white solid. LC-MSD, m/z for C24H18BrN3O4 [M+H]: 492.05 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.4 min

Aufarbeitung

  1. extractionthe aqueous layer was extracted with dichloromethane (3×10 mL)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography
  6. customfurther purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA

Quellen und Nachweise

ORD-Eintrag
ord-a08d2ffff1884c6a989638feb88e8375
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07557213B2

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