Hydrochloric Acid → HCID 22273530, compound

Participants

Reaction Conditions

Reaction Steps

N-Methyl-4-aminobenzenesulphonamide (Method 110; 250 mg, 1.3 mmol) was dissolved in MeOH (3 ml) and 1M HCl in ether (1.3 ml, 1.3 mmol) added. Cyanamide (68 mg, 1.6 mmol) was added along with DMA (0.5 ml). The mixture was heated to 100° C. for 30 min. To this was added 5-(3-dimethylaminoprop-2-en-1-oyl)-1,2-dimethylimidazole (Method 15; 230 mg, 1.2 mmol) and sodium methoxide (150 mg, 2.6 mmol) and heated to 180° C. for 1 hr. The reaction mixture was poured into sat. sodium hydrogen carbonate solution and the resultant solid collected. The solid was triturated with hot DMF and filtered. The filtrate was evaporated in vacuo and purified by flash chromatography on silica gel eluting with DCM/2% methanolic ammonia (100:0 increasing in polarity to 85:15) to yield a white solid which was digested with acetonitrile to yield the title compound as a solid (84 mg, 20%). NMR: 2.38 (d, 6H), 3.95 (s, 3H), 7.19 (d, 2H), 7.63 (s, 1H), 7.68 (d, 2H), 7.93 (d, 2H), 8.43 (d, 1H), 9.91 (s, 1H); m/z 359.

Provenance & Evidence