Triethylamine → HCID 178434757, compound

Participants

Reaction Steps

Example 381, ({trans-3-[2,5-dichloro-4-(pyrrolidin-1-ylmethyl)phenoxy]cyclobutyl}methyl)methylamine (100 mg, 0.29 mmol) and triethylamine (0.04 mL, 0.29 mmol) were dissolved in CH2Cl2 (2 mL). 3,5-Dimethylisoxazole-4-carbonyl chloride (47 mg, 0.29 mmol) was added dropwise under stirring. The mixture was stirred at RT for 3 h and sat. K2CO3 was added. The mixture was stirred at RT for 20 h, dried with Na2SO4, and evaporated. The residue was purified chromatographically (silica gel 40-63 μm, 5 ml, CCl4/CHCl3 100:0→0:100, then CHCl3/MeOH 100:0→95:5). The residue was dissolved in ether (1 mL). 4N HCl/dioxane (0.10 mL) was added, and the reaction mixture was evaporated to dryness, recrystallized from i-PrOH/Et2O. The crystals were separated by filtration and dryed in vacuo to give the title compound (86 mg, 59%) as yellow crystals. LC/MS data: 466.2 (M+H) (calculated for C23H29Cl2N3O3 466.41). 1H NMR-data (DMSO-d6): 10.646 (br.s, 1H, NH+); 7.99 (s, 1H, NH); 6.83-7.24 (m, 1H, Ar—H); 4.66-5.17 (m, 1H), 4.32-4.44 (m, 2H); 3.37-3.72 (m, 4H); 3.03-3.16 (m, 2H); 2.91 (s, 3H); 2.64-2.79 (m, 1H); 2.31-2.43 (m, 4H); 2.11-2.66 (m, 6H); 1.97-2.07 (m, 2H); 1.83-1.94 (m, 2H).

Provenance & Evidence