Ammonium Chloride → HCID 178511416, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of trans [4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexyloxy]-acetonitrile (350 mg, 770 μmol) in a mixture of ethanol (2.5 mL) and water (800 μL) was treated with ammonium chloride (250 mg, 4.60 mmol) and iron powder (170 mg, 3.10 mmol) and heated at 80° C. for 90 minutes. The reaction mixture was hot filtered through Celite® washing several times with ethanol/water. The filtrate was concentrated under vacuum, the residue diluted with water and extracted in to DCM (3×). The combined organic extracts were dried over sodium sulfate and concentrated under vacuum. The iron filter cake was stirred in 20% methanol in DCM, filtered and repeated until no further product was extracted. The combined filtrates were washed with water and the phases separated. The aqueous phase was extracted with DCM (2×). The combined organic extracts were washed with brine, dried over sodium sulfate, concentrated under vacuum and combined with the material isolated above to afford 300 mg (91%) of trans [4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexyloxy]-acetonitrile as a yellow solid. LCMS (Method Q, ESI): RT=2.76 min, m+H=426.1; 1H NMR (400 MHz, CDCl3) δ: 8.14 (m, 2H), 7.83 (s, 1H), 7.53 (t, 1H), 7.49 (d, 1H), 7.45 (t, 2H), 6.52 (d, 1H), 4.72 (d, 1H), 4.30 (s, 2H), 3.73 (m, 1H), 3.58 (m, 1H), 2.80 (br s, 2H), 2.16 (m, 4H), 1.48 (m, 2H), 1.33 (m, 2H).

Provenance & Evidence