Diisopropylethylamine → HCID 178511027, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (3.17 g) in propan-2-ol (32 mL), trans 3-(4-amino-cyclohexyl)-propionitrile trifluoroacetic acid salt (2.75 g, 10.3 mmol) and diisopropylethylamine (4.09 mL, 23.5 mmol) were added. The mixture was stirred at reflux for 16 hours and then cooled to 0° C. The suspension was filtered, and the solid washed with propan-2-ol (×2) and ether, then air dried to afford 3.83 g (90%) of trans 3-[4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexyl]-propionitrile as a bright yellow solid. 1H NMR (400 MHz, CDCl3) δ: 9.10 (s, 1H), 8.99 (d, 1H), 8.19 (d, 2H), 7.66-7.59 (m, 2H), 7.52 (t, 2H), 6.67 (d, 1H), 3.91-3.80 (m, 1H), 2.40 (t, 2H), 2.24 (m, 2H), 1.96 (m, 2H), 1.66 (q, 2H), 1.55-1.39 m, 3H), 1.23-1.10 (m, 2H).

Provenance & Evidence