HCID 178495628, compound → HCID 178495627, compound

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Reaction Steps

A mixture of trans (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(4-methoxymethyl-cyclohexyl)-amine (1.92 g, 4.32 mmol), iron powder (0.96 g, 17.3 mmol) ammonium chloride (1.39 g, 26.0 mmol) and methanol/water (90 mL, 3:1) was stirred and heated at reflux for 1 hour. The cooled mixture was filtered through a pad of Celite® washing the filter cake with methanol. The combined filtrate was concentrated to dryness and the residue dissolved in DCM then purified by column chromatography on silica gel (eluting with 20%-50% ethyl acetate in DCM) affording 1.79 g (99%) of trans 1-benzenesulfonyl-N*4*-(4-methoxymethyl-cyclohexyl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine as a grey solid. LCMS (Method I, ESI): RT=2.49 min, m+H=415.2; 1H NMR (300 MHz, CDCl3): δ 8.14 (d, 2H), 7.81 (s, 1H), 7.57-7.39 (m, 4H), 6.55 (d, 1H), 4.70 (br s, 1H), 3.72-3.55 (m, 1H), 3.35 (s, 3H), 3.24 (d, 2H), 2.22-2.11 (m, 2H), 1.95-1.85 (m, 2H), 1.76-1.50 (m, 3H), 1.33-1.07 (m, 4H).

Provenance & Evidence