1,1'-Carbonyldiimidazole → HCID 178484150, compound

Participants

Reaction Steps

CDI (71 mg, 0.43 mmol) was added to a solution of tetrahydropyran-4-yl-carboxylic acid CAS 5337-03-1 (57 mg, 0.43 mmol) in THF (2 ml) at RT under stirring, the mixture was stirred at RT for 1 h. Example 381, ({trans-3-[2,5-dichloro-4-(pyrrolidin-1-ylmethyl)phenoxy]cyclobutyl}methyl)methylamine (100 mg, 0.29 mmol) was added to the mixture and the solution was stirred at RT for 20 h and evaporated. The residue was purified by chromatography (silica gel, 63-100 μm, 5 g, hexane/CHCl3 20:80→0:100, then CHCl3/MeOH 100:0→95:5). The residue was dissolved in ether (1 mL). 4N HCl/dioxane (0.20 mL) was added, and the reaction mixture was evaporated to dryness. The obtained crystals were washed with ether and dried in vacuo to give the title compound (70 mg, 50% yield). LC/MS data: 455.1 (M+H) (calculated for C23H32Cl2N2O3 455.43). 1H NMR-data (DMSO-d6): 10.64 (br. s, 1H, NH+); 7.88-8.09 (m, 1H, Ar—H); 7.00-7.13 (m, 1H, Ar—H); 4.88-5.37 (m, 1H), 4.32-4.44 (m, 2H); 3.79-3.91 (m, 2H); 3.33-3.56 (m, 6H); 2.98-3.15 (m, 4H); 2.76-2.93 (m, 2H); 2.56-2.65 (m, 1H); 2.10-2.33 (m, 4H); 1.81-2.07 (m, 4H); 1.46-1.69 (m, 4H).

Provenance & Evidence