Triethylamine → HCID 178483879, compound

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Reaction Steps

The compound was synthesized as trifluoroacetate salt starting from trimethyl silyl cyanide (1.88 mL, 20.72 mmol), 5-amino benzimidazole (0.82 g, 6.21 mmol), 4-(3-(dimethylamino)propoxy)benzaldehyde (1.0 g, 5.18 mmol), 10% Pd—C (250 mg), triethylamine (7.5 mL, 51.91 mmol), 1,1′-carbonyldiimidazole (1 g, 6.48 mmol). The product was further purified by prep HPLC using the following conditions: Column: Chiralpak AD-HMobile phase: Hexane: Ethanol (0.1% DEA); Flow rate: 32 mL/min, UV: 210 nm, Diluent: Mobile phase The prep fractions were concentrated in vacuum and partitioned between water and chloroform. The separated organic layer was washed with brine solution. Dried over anhydrous sodium sulphate and concentrated in vacuum to afford 50 mg of the product as brown solid.

Provenance & Evidence