Hydrochloric Acid → HCID 22326757, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 2-chloro-4-isopropoxy-5-cyanopyrimidine (Method 26; 505 mg, 2.56 mmol) and 4-[N-(2-piperidinoethyl)sulphamoyl]aniline (Method 43; 362 mg, 1.28 mmol) in 2-butanol (10 ml) was added 1M HCl in ether (3.6 ml, 3.6 mmol). The reaction was warmed to 70° C. and stirred for 18 hours. The reaction was filtered and the solvent removed under reduced pressure to yield a yellow solid. This solid was partitioned between DCM (40 ml) and 2M sodium hydroxide (40 ml). The phases were separated and the aqueous layer was extracted with DCM (30 ml). The organic phases were combined and washed with water (30 ml) and brine (30 ml). Solvent was removed under reduced pressure and the resulting solid was recrystallized from methanol to give the title compound (15 mg). NMR: 1.35 (m, 2H), 1.45 (m, 10H), 2.25 (m, 6H), 2.85 (m, 2H), 5.45 (m, 1H), 7.30 (br s, 1H), 7.80 (d, 2H), 7.90 (d, 2H),8.75 (s, 1H), 10.60 (br s, 1H); m/z 444.

Provenance & Evidence