N,N-Dimethylethylenediamine → HCID 66717189, compound

Participants

Reaction Conditions

Reaction Steps

2-(3,4-Dimethoxy-phenyl)-5-(2-methanesulfinyl-pyrimidin-5-yl) -imidazo[2,1-b][1,3,4]thiadiazole (66 mg, 0.164 mmol, 1 eq) was dissolved in 1,4-dioxane (min. volume) at 75° C. N,N-dimethylethylenediamine (0.053 ml, 0.493 mmol, 3 eq) was added, and the solution was heated at 85° C. for 4 h. The solvent was removed, and the residue was triturated in Et2O, filtered and washed with more solvent to give the desired product as a pale yellow solid (46 mg, 66%). HPLC-MS: (5-100% B in 8 min, 0.8 mL/min, 50° C.): tR=2.87 min, [M+H]+ m/z 426.3; 1H NMR (300 MHz, CDCl3) δ 8.84 (s, 2H), 7.43-7.38 (m, 3H), 6.93 (d, J=9.0 Hz, 1H), 5.86 (s, 1H), 3.95 (d, J=9.0 Hz, 7H), 3.52 (dd, J=11.4, 5.7 Hz, 2H), 2.56 (t, J=6.0 Hz, 2H), 2.28 (s, 7H) ppm.

Provenance & Evidence