1,2-Diaminocyclohexane, cis- → HCID 117677783, compound

Participants

Reaction Conditions

Reaction Steps

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed tert-butyl (3R)-3-[[5-(4-chloro-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (180.0 mg, 0.32 mmol, 1.00 equiv), cis-1,2-diaminocyclohexane (109.9 mg, 0.96 mmol, 3.00 equiv), sodium 2-methylpropan-2-olate (61.5 mg, 0.64 mmol, 2.00 equiv) and toluene (8.0 mL). tris(dibenzylideneacetone)dipalladium (30.0 mg, 0.03 mmol, 0.10 equiv), and o-biphenyl(t-Bu)2P (19.1 mg, 0.06 mmol, 0.20 equiv) were added. And nitrogen was bubbled in for 5 min. The resulting mixture was stirred for 12 h at 95° C. in an oil bath. After cooled down, the reaction mixture was quenched by the addition of 30.0 mL of water, and extracted with ethyl acetate (3×30.0 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtered and concentrated under reduced pressure, the residue was purified by flash chromatography on silica gel, eluting with a mixture of 10-100% ethyl acetate in petroleum ether to give the title compounds as a white solid. MS m/z [M+H]+ (ESI): 639.

Provenance & Evidence