Toluene → HCID 117926390, compound

Participants

Reaction Steps

A mixture of 6-benzyl-8-(pyridin-2-yl)pyrido[2,3-d]pyridazin-5(6H)-one RL-10 (45 mg, 0.143 mmol), 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (57 mg, 0.143 mmol), and 4 mL of toluene were heated to 115° C. for 2 h. Another 35 mg aliquot of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide was added and the heating was continued for 2 h. Still another 35 mg aliquot of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide was added and heating continued for an additional 2 h. After cooling, the reaction mixture was poured into 15 mL of saturated brine and then extracted with 4×20 mL of ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and dried overnight at 60° C. under vacuum to give 6-benzyl-8-(pyridine-2-yl)pyrido[2,3-d]pyridazine-5(6H)-thione RL-11 (31 mg, 0.94 mmol). 1H NMR (400 MHz, Chloroform-d) δ 9.25 (dd, J=8.4, 1.7 Hz, 1H), 9.19-9.12 (m, 1H), 9.03 (s, 1H), 8.13 (bd, J=57.3 Hz, 1H), 7.72 (dd, J=8.4, 4.4 Hz, 1H), 7.64-7.52 (m, 3H), 7.40-7.25 (m, 4H), 6.17 (s, 2H). LCMS: (M+H)+, 331.

Provenance & Evidence