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Sodium Chloride → 5-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid pyrrolidin-1-ylamide

HRID 1695338
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1695338
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([C:20]([OH:22])=O)[NH:18][N:19]=3)=[C:11]([CH3:23])[O:10][N:9]=2)=[CH:4][CH:3]=1.F[B-](F)(F)F.[N:29]1(OC(N(C)C)=[N+](C)C)[C:33]2[CH:34]=[CH:35][CH:36]=CC=2N=[N:30]1.C(N(CC)C(C)C)(C)C.Cl.NN1CCCC1.[Cl-].[Na+]>CN(C=O)C>[N:29]1([NH:30][C:20]([C:17]2[NH:18][N:19]=[C:15]([O:14][CH2:13][C:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[N:9][O:10][C:11]=3[CH3:23])[CH:16]=2)=[O:22])[CH2:33][CH2:34][CH2:35][CH2:36]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 3017392Pyrrolidin-1-amine monohydrochlorideHCID 666436795-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid

Produkt 1

HCID 49792922
5-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid pyrrolidin-1-ylamide
Ausbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid (100 mg, 0.32 mmol) in DMF (5 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (152 mg, 0.47 mmol), N,N-diisopropyl ethyl amine (270 μL, 1.6 mmol) and N-aminopyrrolidine HCl (58 mg, 0.47 mmol). The resulting reaction mixture was stirred overnight at room temperature. The reaction mixture was then poured into aqueous sodium chloride (saturated) and extracted with ethyl acetate. The combined organic layers were then washed with water, citric acid solution and saturated sodium hydrogen carbonate solution and then dried over sodium sulfate, filtered and evaporated. Concentration and purification by chromatography (silica, dichloromethane:methanol=100:0 to 9:1) afforded the title compound (91 mg, 75%) as a white solid. MS: m/e=386.2 [M+H]+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were then washed with water, citric acid solution and saturated sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. concentrationConcentration and purification by chromatography (silica, dichloromethane:methanol=100:0 to 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-f7080502f4174adaa74fb697d30a87c9
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163728B2

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