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Ammonium Chloride → 4-[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)-N-(methylsulfonyl)benzamide

HRID 1620314
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1620314
[Cl:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][C:14]=2[C:22]2[C:23]([O:28][CH3:29])=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:40][S:41](Cl)(=[O:43])=[O:42].[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:19][S:41]([CH3:40])(=[O:43])=[O:42])=[O:18])=[CH:15][C:14]=2[C:22]2[C:23]([O:28][CH3:29])=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 2733832Lithium hexamethyldisilazaneHCID 666666844-[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)benzamide

Produkt 1

HCID 566030494-[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)-N-(methylsulfonyl)benzamideAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-[(5-chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)benzamide (Preparation 27, 436 mg, 1.05 mmol) in anhydrous THF (10.0 mL) was added lithium bis(trimethylsilyl) amide (1.0 M in THF, 2.63 mL, 2.63 mmol). The solution was stirred for 30 minutes before the addition of methanesulfonyl chloride (210 uL, 2.63 mmol). The reaction mixture was stirred for 1 hour and then a saturated aqueous solution of ammonium chloride (25 mL) was added to the reaction mixture. The reaction mixture was partitioned between water (30 mL) and EtOAc (25 mL). The aqueous phase was separated and extracted with EtOAc (2×25 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a solid. The material was purified by silica gel column chromatography, eluting with 60:40:1 heptane/EtOAc/acetic acid. Fractions containing product were combined and concentrated in vacuo to obtain the title compound as a solid (230 mg):

Aufarbeitung

  1. customThe reaction mixture was partitioned between water (30 mL) and EtOAc (25 mL)
  2. customThe aqueous phase was separated
  3. extractionextracted with EtOAc (2×25 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a solid
  8. customThe material was purified by silica gel column chromatography
  9. washeluting with 60:40:1 heptane/EtOAc/acetic acid
  10. additionFractions containing product
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-40f9ca284e594020ad5dcd24f6ec7e78
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08772343B2

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