Ammonia → HCID 59536352, compound

Participants

Reaction Steps

A solution of 1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.5 g, 2 mmol) (Example 9, step 3) in dry tetrahydrofuran (10 mL) was treated with 1,1′-thiocarbonyldiimidazole (0.5 g, 3 mmol) and stirred at RT for 4 h. The solvent was removed and the resulting residue was dissolved in ammonia (2.0 M solution in methanol, 15 mL, 30 mmol) and stirred the resulting solution in a pressure tube at RT for 1 h followed by heating at 55° C. for 5 h. The solvent was removed under vacuum and the residue was purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/H2O (0.1% TFA)] to give 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carbothioamide as a white solid. MS (ESI, pos. ion) m/z: 337 (M+1).

Provenance & Evidence