Triethylamine → HCID 178434755, compound

Participants

Reaction Steps

Example 386, ({trans-3-[2-Chloro-3-(pyrrolidin-1-ylmethyl)phenoxy]cyclobutyl}methyl) amine (200 mg, 0.7 mmol) and triethylamine (0.1 mL, 0.7 mmol) were dissolved in CH2Cl2 (2 mL). 3,5-Dimethylisoxazole-4-carbonyl chloride (109 mg, 0.7 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, 3 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 (170 mg, 55%) as yellow crystals. LC/MS data: 418.1 (M+H) (calculated for C22H28ClN3O3 417.94). 1H NMR-data (DMSO-d6): 10.36 (br.s, 1H, NH+); 7.87-8.40 (m, 1H, NH); 7.30-7.44 (m, 2H, Ar—H); 6.96-7.04 (m, 1H, Ar—H); 4.88-5.00 (m, 1H), 4.46-4.52 (m, 2H); 3.35-3.48 (m, 4H); 3.08-3.19 (m, 2H); 2.52-2.62 (m, 1H); 2.48 (s, 3H); 2.31-2.40 (m, 2H); 2.28 (s, 3H); 2.13-2.23 (m, 2H); 1.97-2.10 (m, 2H); 1.83-1.94 (m, 2H).

Provenance & Evidence