1,2,4-Thiadiazol-5-amine--hydrogen chloride (1/1) → HCID 59466402, Verbindung

HRID 1696103

Reaktionsgleichung

Reaktionsgleichung von HRID 1696103
Cl.[S:2]1[C:6]([NH2:7])=[N:5][CH:4]=[N:3]1.[O:8]=[C:9]1[CH2:14][N:13]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:12][CH2:11][N:10]1[C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1>[O:8]=[C:9]1[CH2:14][N:13]([C:15](=[O:20])[C:16]([F:18])([F:17])[F:19])[CH2:12][CH2:11][N:10]1[C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH:7][C:6]2[S:2][N:3]=[CH:4][N:5]=2)(=[O:29])=[O:28])=[CH:25][CH:26]=1

Komponenten

4

Edukt 2

HCID 220145431,2,4-Thiadiazol-5-amine--hydrogen chloride (1/1)HCID 59465974HCID 59465974, Verbindung

Produkt 1

HCID 59466402HCID 59466402, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Synthesized according to general procedure 12, method A. The reaction was set up with 1,2,4-Thiadiazol-5-ylamine hydrochloride (0.56 g, 4.0 mmol), anhydrous pyridine (3.5 mL), and 4-(2-oxo-4-(2,2,2-trifluoroacetyl)piperazin-1-yl)benzene-1-sulfonyl chloride (1.5 g, 4.0 mmol). The dark oil was purified via silica gel chromatography using 5% MeOH in CH2Cl2 followed by a second purification on silica gel using 80% EtOAc in hexanes to obtain the desired sulfonamide as a white solid (0.73 g, 1.92 mmol, 48% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=436.1; tR=2.27 min.

Aufarbeitung

  1. customSynthesized
  2. customThe dark oil was purified via silica gel chromatography
  3. customfollowed by a second purification on silica gel using 80% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d6c00f8373474349ae3194d58c284a01
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163720B2

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