1,4-Dioxane → HCID 57377355, Verbindung

HRID 72556

Reaktionsgleichung

Reaktionsgleichung von HRID 72556
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:28][CH2:27][CH:26]([CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)[CH2:25]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].O1CCOCC1.O.[OH-].[Li+]>O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:28][CH2:27][CH:26]([CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)[CH2:25]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8]

Komponenten

5

Edukt 3

HCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 67958339Methyl 4-(1-(5-chloro-2-(3-((3-fluorophenoxy)methyl)pyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoate

Produkt 1

HCID 57377355HCID 57377355, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-(1-(5-chloro-2-(3-((3-fluorophenoxy)methyl)pyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoate (D200) (37 mg, 0.070 mmol) in a mixture 1,4-dioxane and water (3:1) (2 ml) lithium hydroxide monohydrate (10 mg, 0.238 mmol) was added and the mixture was stirred 20 min (4 cycles of 5 min each) under microwaves irradiation. After solvent evaporation the residue was diluted with water (5 ml) and 1M HCl (5 ml) and extracted with ethylacetate (3×10 ml). Collected organics after solvent evaporation afforded a residue that was purified by ISOLUTE Spe-Si (1 g) eluting with a mixture dichloromethane/methanol 98:2. Collected fractions after solvent evaporation afforded the title compound (E76) (18.2 mg)

Aufarbeitung

  1. customunder microwaves irradiation
  2. customAfter solvent evaporation the residue
  3. additionwas diluted with water (5 ml) and 1M HCl (5 ml)
  4. extractionextracted with ethylacetate (3×10 ml)
  5. customCollected organics after solvent evaporation
  6. customafforded a residue that
  7. customwas purified by ISOLUTE Spe-Si (1 g)
  8. washeluting with a mixture dichloromethane/methanol 98:2
  9. customCollected fractions after solvent evaporation

Quellen und Nachweise

ORD-Eintrag
ord-75ba6ba62431407f8959d271c8005641
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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