Trifluoroacetic anhydride → N-{2-[5-(2-Cyanoethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

HRID 1851548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851548
[CH3:1][N:2]([S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19]([NH2:21])=O)=[CH:15][N:16]=1)=[CH:8]2.FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[C:19]([CH2:18][CH2:17][C:14]1[S:13][C:12]([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[CH:4][C:3]=3[N:2]([CH3:1])[S:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)(=[O:24])=[O:23])=[N:16][CH:15]=1)#[N:21]

Komponenten

4

Edukt 2

HCID 9845Trifluoroacetic anhydrideHCID 57901592HCID 57901592, Verbindung

Produkt 1

HCID 57901663N-{2-[5-(2-Cyanoethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a mixture of 3-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)propanamide (1.32 g) and pyridine (15 mL) was added trifluoroacetic anhydride (0.90 mL) at 0° C. over 15 min. The reaction mixture was stirred at room temperature for 2 hr and concentrated. 10% Aqueous citric acid solution was added to the residue. The resulting crystals were collected by filtration, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (1.20 g, yield 95%) was obtained as yellow crystals from a fraction eluted with tetrahydrofuran-hexane (2:1, volume ratio). melting point 207-208° C.

Aufarbeitung

  1. concentrationconcentrated
  2. addition10% Aqueous citric acid solution was added to the residue
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-11ca78c5e3fc4d7a807cc92f6955fd30
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957070B2

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