Dimethylformamide → HCID 178512214, compound

Participants

Reaction Steps

To a solution of 150 mg (0.23 mmol) 99 in 5 mL DMF 336.4 mg (2.3 mmol) pyrazole-1-carboxamidine hydrochloride and 396 μL (2.3 mmol) diisopropylethylamine was added. The solution was stirred overnight at ambient temperature. Next morning the solvent was evaporated, the oily residue was dissolved in 20 mL aqueous 0.1% TFA solution and was purified on a preparative reverse phase HPLC column using acetonitrile gradient. The fractions containing the pure product were pooled, evaporated to dryness dissolved in 3 mL methanol and treated with 1 mL 4.0M HCl in dioxane. 100 was precipitated with ether as bis-HCl salt, filtered off and dried to yield 62 mg (49%). MS: 241.70 (M+2H+). 1H-NMR (DMSO d6) 10.22 (s, 1H); 8.72 (s, 2H); 8.61 (t, 1H); 8.38 (s, 2H); 8.02 (t, 1H); 7.72 (s, 4H); 7.52 (t, 1H); 7.11 (d, 3H); 6.70 (d, 2H); 3.85 (d, 2H); 3.26–3.08 (m); 2.34 (m, 2H); 0.90 (m, 2H); 0.19–0.0 (m, 4H);

Provenance & Evidence