HCID 67457507, compound → HCID 49771654, compound

Participants

Reaction Steps

[2-Amino-6-(2-fluoro-phenyl)-3-nitro-pyridin-4-yl]-benzyl-carbamic acid ethyl ester (31 mg) was dissolved in acetic acid (1 ml). Zinc powder (Aldrich, 99%, 20 mg) was added and the mixture left to stir at room temperature under nitrogen for 2 hours. Additional zinc powder (30 mg) was added and mixture left to stir for a further 1 hour. The reaction mixture was diluted with methanol (2 ml) then filtered directly onto a cation exchange cartridge (Bakerbond SCX, sulphonic acid bonded-phase, 1 g). The SCX cartridge was washed with methanol (2×5 ml) to remove impurities and then the product was released with ammonia in methanol (2 M, 5 ml). The desired fraction was evaporated to a pale brown solid. This was triturated with ethyl acetate then filtered and washed with more ethyl acetate to yield the title compound (8 mg) as a pale purple solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.99 (s, 2 H) 5.82 (s, 2 H) 6.87 (d, J=1.95 Hz, 1 H) 7.15-7.29 (m, 3 H) 7.29-7.39 (m, 5 H) 7.81 (td, J=8.01, 1.95 Hz, 1 H) 10.51 (s, 1 H), LCMS Rt=2.21 m/z 335 [MH]+

Provenance & Evidence