Ammonium Chloride → HCID 178507999, compound

Participants

Reaction Conditions

Reaction Steps

Crude trans 4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanol (65.0 g, approx. 148 mmol) was suspended in ethanol (1000 mL, IMS grade) and water (300 mL). Ammonium chloride (47.5 g, 888 mmol) was added, and the mixture was stirred at 50° C. Powdered iron (33.0 g, 592 mmol) was added slowly and the resulting mixture was stirred at reflux for 2 h, then cooled to room temperature. The mixture was filtered and the filter cake washed with further ethanol, then the combined filtrate was concentrated under vacuum. The residue was suspended in water and extracted with dichloromethane (×2) and the combined organic extracts were dried (Na2SO4) and concentrated under vacuum. The residue was triturated with methanol then water to give 19.0 g (33%) of trans 4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanol. The methanol mother liquor was concentrated and the resulting residue triturated with acetonitrile to give a further 11.0 g (19%) of trans 4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanol. NMR (400 MHz, DMSO) δ: 8.04 (m, 2H), 7.68 (m, 2H), 7.59 (m, 3H), 6.76 (d, 1H), 5.68 (br s, 1H), 3.71 (br s, 1H), 1.91 (m, 2H), 1.84 (m, 2H), 1.34 (m, 4H), further signals partially obscured residual water peak.

Provenance & Evidence