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Pyridine → 4-tert-Butyl-N-{4-chloro-2-[4-methyl-5-(5-methyl-oxazol-4-yl)-4H-[1,2,4]triazol-3-yl]-phenyl}-benzenesulfonamide

HRID 448108
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 448108
[CH3:1][NH:2][C:3]([C:5]1[N:6]=[CH:7][O:8][C:9]=1[CH3:10])=O.N1C=CC=CC=1.[C:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[C:38]([NH:40][NH2:41])=O)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>ClCCl>[C:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[C:38]2[N:2]([CH3:1])[C:3]([C:5]3[N:6]=[CH:7][O:8][C:9]=3[CH3:10])=[N:41][N:40]=2)(=[O:28])=[O:29])=[CH:23][CH:22]=1)([CH3:18])([CH3:19])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 593029884-tert-butyl-N-(4-chloro-2-hydrazinocarbonyl-phenyl)benzenesulfonamideHCID 59303069N,5-Dimethyloxazole-4-carboxamide

Produkt 1

HCID 593030164-tert-Butyl-N-{4-chloro-2-[4-methyl-5-(5-methyl-oxazol-4-yl)-4H-[1,2,4]triazol-3-yl]-phenyl}-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

A vial was charged with 5-methyl-oxazole-4-carboxylic acid methylamide (71 mg, 0.5 mmol), pyridine (0.12 mL, 1.5 mmol), and anhydrous dichloromethane (2.5 mL). The reaction vessel was cooled to −40° C. and trifluoromethanesulfonyl anhydride (0.11 mL, 0.65 mmol) was added. The reaction was subsequently warmed to −10° C. over 2.5 h and then 4-tert-butyl-N-(4-chloro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide (191 mg, 0.5 mmol) was added. The reaction was warmed to room temperature stirred an additional 2 h. The solvent was concentrated in vacuo and ethanol (5 mL) and diisopropylamine (0.5 mL) were added and the solution stirred at 90° C. overnight. The following day, the reaction was concentrated in vacuo and the crude material was purified by flash column chromatography (10-100% ethyl acetate and hexane), followed by preparative HPLC (10-90% gradient of MeCN-water) to yield the title compound: MS (ES) M+H expected 486.1, found 486.0.

Aufarbeitung

  1. temperatureThe reaction was subsequently warmed to −10° C. over 2.5 h
  2. temperatureThe reaction was warmed to room temperature
  3. concentrationThe solvent was concentrated in vacuo and ethanol (5 mL) and diisopropylamine (0.5 mL)
  4. additionwere added
  5. stirringthe solution stirred at 90° C. overnight
  6. concentrationThe following day, the reaction was concentrated in vacuo
  7. customthe crude material was purified by flash column chromatography (10-100% ethyl acetate and hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c5051160591542a4bf8cff860143099b
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08481579B2

Notizen zur Reaktion

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