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Triethylamine → N-[3-(3-Fluorophenyl)-1H-5-indazolyl]methanesulfonamide

HRID 503147
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 503147
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OC(C)(C)C)=O)[N:6]=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>O1CCCC1.O>[F:24][C:20]1[CH:19]=[C:18]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[CH:3]=3)[NH:7][N:6]=2)[CH:23]=[CH:22][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222606241h-Indazole-1-carboxylic acid,5-amino-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

Produkt 1

HCID 22260964N-[3-(3-Fluorophenyl)-1H-5-indazolyl]methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of 50 mg of tert-butyl 5-amino-3-(3-fluorophenyl)-1H-1-indazolecarboxylate produced in Production Example I-26 in 2 ml tetrahydrofuran were added 30 μl of triethylamine and 15 μl of methanesulfonyl chloride, and the mixture was stirred at room temperature for 10 hours. The reaction mixture was diluted with water and was extracted with ethyl acetate. The organic layer was sequentially washed with 1 N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The resulting crude crystals were recrystallized from ethyl acetate-diethyl ether, to give 26 mg of the title compound as a colorless powder.

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was sequentially washed with 1 N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed
  5. customThe resulting crude crystals were recrystallized from ethyl acetate-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5968333e2aca43a5a5a3e1f27c89a784
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07776890B2

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