1,1'-Carbonyldiimidazole → HCID 178484139, compound

Participants

Reaction Steps

CDI (110 mg, 0.70 mmol) was added to a solution of tetrahydropyran-4-yl-carboxylic acid CAS 5337-03-1 (132 mg, 1.0 mmol) in THF (2 ml) at RT under stirring, the mixture was stirred at RT for 1 h. Example 386, ({trans-3-[2-Chloro-3-(pyrrolidin-1-ylmethyl)phenoxy]cyclobutyl}methyl) amine (200 mg, 0.7 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 (162 mg, 53% yield). LC/MS data: 407.1 (M+H) (calculated for C22H31ClN2O3 406.96). 1H NMR-data (DMSO-d6): 10.31 (br. s, 1H, NH+); 7.73-8.12 (m, 1H, NH); 7.30-7.44 (m, 2H, Ar—H); 6.94-7.04 (m, 1H, Ar—H); 4.78-4.95 (m, 1H), 4.42-4.58 (m, 2H); 3.79-3.91 (m, 2H); 3.41-3.49 (m, 2H+ H2O); 3.25-3.34 (m, 2H); 3.09-3.24 (m, 4H); 2.24-2.45 (m, 4H); 1.98-2.19 (m, 4H); 1.83-1.94 (m, 2H); 1.83-1.94 (m, 4H).

Provenance & Evidence