Ammonium Chloride → HCID 178511272, compound

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Reaction Steps

A suspension of trans 4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanecarbonitrile (5.00 g, 11.8 mmol), iron powder (−325 mesh, 2.59 g, 47.0 mmol) and ammonium chloride (3.74 g, 70.5 mmol) in a mixture of ethanol and water (3:1, 400 mL) was mechanically stirred at reflux for 4 hours. The cooled mixture was filtered through Celite®. The filtrate was concentrated under vacuum to low volume and the residue extracted into DCM (3×). The combined extracts were washed with water and brine, dried over sodium sulphate and concentrated under vacuum. Purification by diethyl ether trituration afforded 4.51 g (97%) of trans 4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanecarbonitrile as a light grey solid. LCMS (Method Q, ESI): RT=2.69 min, m+H=396.1; 1H NMR (400 MHz, DMSO) δ: 8.02 (dd, 2H), 7.65 (m, 1H), 7.57 (m, 3H), 7.47 (d, 1H), 6.76 (d, 1H), 5.09 (d, 2H), 4.36 (s, 2H), 3.76 (m, 2H), 2.70 (m, 1H), 2.04 (dd, 2H), 1.94 (m, 2H), 1.72 (m, 2H), 1.29 (m, 2H).

Provenance & Evidence