racemic trans [3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentyl]-carbamic acid tert-butyl ester → racemic trans [3-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentyl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of racemic trans [3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentyl]-carbamic acid tert-butyl ester (23.7 g, 47.2 mmol) and palladium hydroxide (2.44 g, 20%) in acetic acid (285 mL) was stirred under an atmosphere of hydrogen at 50° C. for 3 hours and then room temperature for 18 hours. The mixture was filtered through Celite® and then concentrated in vacuo. The residue was dissolved in DCM, then washed (saturated sodium hydrogen carbonate solution (3×) and brine) and concentrated to dryness. Purification by column chromatography on silica gel (gradient: DCM to ethyl acetate) afforded 11.6 g (52%) of racemic trans [3-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentyl]-carbamic acid tert-butyl ester as a purple solid. LCMS (Method B, ESI): RT=2.85 min, m+H=472.4; 1H NMR (400 MHz, DMSO) δ: 8.00 (d, 2H), 7.66 (t, 1H), 7.57 (t, 2H), 7.52 (s, 1H), 7.45 (d, 1H), 6.97 (d, 1H), 6.82 (d, 1H), 5.21 (d, 1H), 4.35 (m, 3H), 3.95 (m, 1H), 2.13-1.91 (m, 2H), 1.79 (m, 2H), 1.44 (m, 2H), 1.37 (s, 9H).

Provenance & Evidence