Triethylamine → (3-{[(6-Oxo-5,6-dihydro-phenanthridin-2-ylcarbamoyl)-methyl]-amino}-propyl)-carbamic acid tert-butyl ester

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Reaction Steps

To a stirred suspension of 2-chloro-N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-acetamide (XXIV, Lg=Cl) (50 mg, 0.17 mmol) in N,N-dimethylformamide (2 mL), (3-amino-propyl)-carbamic acid tert-butyl ester (0.09 mL, 0.51 mmol) and triethylamine (0.036 mL, 0.26 mmol) were added. The reaction mixture was stirred at room temperature overnight, evaporated to dryness and then purified through by preparative HPLC on a Waters X Terra RP 18 (19×250 mm, 5 μm) column. Mobile phase A was 0.05% ammonium hydroxide/acetonitrile:95/5 and mobile phase B was acetonitrile/water:95/5. Gradient from 10 to 75% B in 15 min. Fractions containing the desired compound were dried, affording 32 mg (44% yield) of (3-{[(6-oxo-5,6-dihydro-phenanthridin-2-ylcarbamoyl)-methyl]-amino}-propyl)-carbamic acid tert-butyl ester.

Provenance & Evidence