1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 89726458, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-bromo-1,3-thiazole-4-carboxylate (10 g) in MeCN (120 mL) was added 1-Boc-piperazine (8.56 g) followed by DBU (10.1 mL). The resulting solution was stirred at 80° C. for 5 h. The reaction mixture was diluted with EA and water. The layers were separated and the org. phase was further washed with water. The combined aq. layers were extracted with EA. The combined org. layers were dried over Na2SO4, filtrated off and evaporated in vacuo. The crude was purified by CC (Biotage, SNAP 100 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 10 for 2CV, 10 to 50 over 12CV, 50 for 3CV) to afford 7.65 g of yellow oil. LC-MS (B): tR=0.79 min; [M+H]+: 328.37.

Provenance & Evidence