HCID 117701942, compound → (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

(1S,2S,3R,4R)-3-(2-Amino-5-chloro-3-nitro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (100 mg, 0.3 mmol) was dissolved in a mixture of tetrahydrofuran (1 mL) and acetic acid (1.6 mL). Powdered iron (121 mg, 2.162 mmol) was added and the mixture was stirred at 30° C. for four hours. Two drops of water was added and suspended solids were removed by filtration. The solid was washed with ethyl acetate (5 mL) and the combined filtrates were portioned between ethyl acetate and saturated sodium bicarbonate solution. The organics were extracted with ethyl acetate (3×25 mL), were dried (sodium sulfate) and were concentrated. Purification was effected via ISCO chromatography (12 g silica cartridge: gradient elution—0 to 15% MeOH:DCM) to afford 77 mg (80%) of the title compound as a tan solid. 1H NMR (d-chloroform): 7.49 (s, 1H), 6.18-6.20 (m, 4H), 6.09 (m, 1H), 4.51 (d, J=11 Hz, 1H), 4.09 (br s, 2H), 3.79 (d, J=9 Hz, 1H), 2.97 (s, 1H), 2.64 (s, 1H), 2.53 (d, J=8 Hz, 1H), 2.32 (d, J=9 Hz, 1H), 2.06 (s, 1H), 1.66 (d, J=9 Hz, 1H). MS: 294.99 (M+H). HPLC retention time: 1.62 minutes (G Method).

Provenance & Evidence