Diisopropylethylamine → HCID 67383963, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-Fluoromethoxy-phenyl)-imidazo[1,2-c]pyrimidin-7-ylamine (100 mg, 0.387 μmol) was combined with EtOAc (2.0 ml) to give a light yellow suspension. 4-(Azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (97 mg, 465 μmol) and DIPEA (300 mg, 406 μl, 2.32 mmol) were added. The reaction mixture was cooled down to 0° C. and n-propylphosphonic acid anhydride, cyclic trimer (616 mg, 582 μl, 968 μmol) was added drop by drop. After stirring at 0° C. for 30 min the reaction mixture was allowed to warm-up and stirred at RT overnight. The reaction mixture was then diluted with and 10% NaHCO3 aq. solution and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4) and concentrated under vacuum. The crude product was purified by flash chromatography (10 g SiO2; eluent: CH2Cl2 to CH2Cl2/MeOH/NH3 140:10:1). The obtain material was dissolved in CH2Cl2 and the product was precipitated with Et2O, filtered off, washed with Et2O, and dried overnight at HV. Yellow solid (89 mg, 47%). MS (m/z)=450.2 [M+H+].

Provenance & Evidence