Water → HCID 22037815, compound

Participants

Reaction Steps

A mixture of 1-cyclopentyl-1H-pyrrolo[2,3-d]pyridazin-4-amine (0.595 mg, approx. 60% pure, 1.76 mmol) in dichloromethane (100 mL) was treated with a solution of dichloromethane (5 mL) containing bromine (0.5 g, 2.95 mmol) over the course of 1.25 hours. The mixture was stirred an additional one hour then another portion of dichloromethane (3 mL) containing bromine (0.3 g) was added. The mixture was stirred for 2.5 hours then treated with 5 mL 5N aqueous sodium hydroxide and 25 mL water. The layers were separated and the organic layer was concentrated under reduced pressure to give a residue which was purified by reverse phase preparative HPLC to give 3-bromo-1-cyclopentyl-1H-pyrrolo[2,3-d]pyridazin-4-amine (168 mg, 35%); 1H NMR (DMSO-d6, 400 MHz) δ 8.94 (s, 1H), 7.79 (s, 1H), 6.11 (bs, 2H), 4.94 (m, 1H), 2.12 (m, 2H), 1.83 (m, 4H), 1.67 (m, 2H); 5%–100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 11.25 min.; LC/MS: MH+ 282.8.

Provenance & Evidence