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Lithium hexamethyldisilazane → 2-(2H-1,2,3-Triazol-2-yl)-N-[(1S,2R)-2-{[5-(trifluoromethyl)pyrazin-2-yl]oxy}cyclopentyl]benzamide

HRID 1750589
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1750589
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[OH:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][C@@H:13]1[NH:17][C:18](=[O:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[N:29]=[CH:28][CH:27]=[N:26]1.Cl[C:32]1[CH:37]=[N:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][N:33]=1>C1COCC1>[N:29]1[N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([NH:17][C@H:13]2[CH2:14][CH2:15][CH2:16][C@H:12]2[O:11][C:32]2[CH:37]=[N:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][N:33]=2)=[O:30])[N:26]=[CH:27][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 2733832Lithium hexamethyldisilazaneHCID 189876452-Chloro-5-(trifluoromethyl)pyrazineHCID 118308343N-[(1S,2R)-2-Hydroxycyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide2×

Produkt 1

HCID 1183082052-(2H-1,2,3-Triazol-2-yl)-N-[(1S,2R)-2-{[5-(trifluoromethyl)pyrazin-2-yl]oxy}cyclopentyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

LiHMDS in THF (1.0 M, 0.477 ml, 0.477 mmol) was added to a solution of N-[(1S,2R)-2-hydroxycyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Intermediate 10; 0.100 g, 0.37 mmol) in THF (3 ml) at 0° C. under nitrogen. The reaction was stirred at this temperature for 1 hour and then 2-chloro-5-(trifluoromethyl)pyrazine (CAS number 799557-87-2; 0.059 ml, 0.48 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 5 hours. The reaction was then quenched with water (2 ml) and extracted with ethyl acetate (30 ml). The organics were washed with brine (10 ml), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-50% ethyl acetate/petrol) to afford the title compound.

Aufarbeitung

  1. stirringstirred for 5 hours
  2. customThe reaction was then quenched with water (2 ml)
  3. extractionextracted with ethyl acetate (30 ml)
  4. washThe organics were washed with brine (10 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (silica, 0-50% ethyl acetate/petrol)

Quellen und Nachweise

ORD-Eintrag
ord-8f487996b46848edb81efafb706f5659
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156829B2

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