1,1'-Carbonyldiimidazole → HCID 57585130, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(6-chloro-5-(dimethylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (95 mg, 312 μmol) and CDI (110 mg, 678 μmol) in DMF (1 mL) was heated at 60° C. After sitting overnight, more reagent was added and the mixture was heated for 4 h. 2-morpholinoethanamine (300 μL, 2286 μmol) was added to the mixture, a solution formed. After 3 h, the mixture was cooled to rt and diluted with DCM (15 mL). The solution was washed with H2O (15 mL), dried over Na2SO4 and concentrated. The crude oil was purified by silica gel chromatography with 0-5% (2 N NH3-MeOH) in DCM to give the product as a white powder after hexane washing (45 mg, 31%). MS (ESI, POS. ION) M/Z: calc'd for C21H25ClN6O2S: 460.1. found: 461.1. 1H NMR (400 MHz, chloroform-d) δ ppm 2.49-2.70 (m, 6H) 2.92 (s, 6H) 3.49-3.59 (m, 2H) 3.71-3.83 (m, 4H) 7.49 (s, 1H) 7.56 (d, J=8.03 Hz, 1H) 7.79 (d, J=8.53 Hz, 1H) 7.90 (s, 1H) 8.24 (s, 1H).

Provenance & Evidence