Water → HCID 70232275, Verbindung

Reaktionsgleichung

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[S:4][C:3]=1[C:19]([NH2:21])=[O:20].C(N(CC)CC)C.O.[O:30]1CCC[CH2:31]1>>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9]2[C:10]3[C:2]4[NH:1][C:31](=[O:30])[NH:21][C:19](=[O:20])[C:3]=4[S:4][C:5]=3[CH:6]=[N:7][CH:8]=2)=[CH:17][CH:16]=1

Komponenten

Edukt 4

HCID 962Water

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 9923070HCID 9923070, Verbindung

Produkt 1

HCID 70232275HCID 70232275, VerbindungAusbeute 51 %

Versuchsvorschrift

To a suspension of Example 131D (70mg, 0.22 mmol) in anhydrous tetrahydrofuran (5 mL) under nitrogen atmosphere was added 1,1-carbonyldiimidazole (71mg, 0.44 mmol) and triethylamine (60 [μL, 0.44 mmol). The reaction mixture was stirred at reflux for 48 hours and then ambient temperature for an additional 24 hours. The reaction mixture was poured into a 1:1 solution of water: saturated NH4Cl and the resulting solid collected by filtration. This material was purified by flash chromatography on silica gel eluting with 20% acetone-hexane. The desired fractions were combined, evaporated and slurried in hot EtOAC to obtain title compound (39 mg) in 51% yield.