N-(1,1-dimethyl-2-morpholin-4-ylethyl)-2-{5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetamide → N-(1,1-dimethyl-2-morpholin-4-ylethyl)-2-[5-(4-fluorobenzyl)-3-(1H-1,2,3-triazol-4-yl)-1H-pyrazol-1-yl]acetamide

Participants

Reaction Steps

A solution of N-(1,1-dimethyl-2-morpholin-4-ylethyl)-2-{5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetamide (1.3 g, 2.31 mmol) in TFA (30 mL) was refluxed overnight. The mixture was concentrated in vacuo and the residue was treated with water (30 mL) and CH2Cl2 (40 mL). The mixture was adjusted to pH 8-9 with Et3N. The organic layer was separated, dried over Na2SO4 and concentrated. The residue was purified via prep. HPLC to yield the title compound (380 mg, 38%) as yellow syrup. 1H NMR (400 MHz, MeOD) δ ppm 8.003 (s, 1H), 7.322 (m, 2 H), 7.100 (m 2 H), 6.399 (s, 1 H), 4.916 (m, 3 H), 4.089 (s, 2 H), 3.899-3.189 (m, 9 H), 1.472 (s, 6 H).

Provenance & Evidence