Triethylamine → HCID 21865179, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclohexylacetic acid (0.16 g, 1.1 mmol, Aldrich) in CH2Cl2 (5 mL) and DMF (2 drops) was added oxalyl chloride (0.84 mL, 1.7 mmol, 2 M solution in CH2Cl2, Aldrich) dropwise. After the addition was complete and gas evolution ceased, the reaction mixture was heated at 40° C. for 30 min. The excess oxalyl chloride and CH2Cl2 was evaporated in vacuum to provide a yellow oil. The oil was added dropwise to a solution of N-{4-[6-(2-amino-4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide, (Example 151), (0.25 g, 0.56 mmol) in acetone (15 mL) and triethylamine (0.20 mL, 1.7 mmol, Aldrich) at room temperature. The reaction mixture was stirred for 16 h and then concentrated in vacuum. The residue was dissolved in EtOAc (10 mL) and washed with satd NaHCO3 (2×20 mL), dried over Na2SO4, filtered and concentrated in vacuum. Purification by silica gel chromatography (1:1:0.5 CH2Cl2/hexanes/EtOAc) provided the title compound as a white crystalline solid. Mp: 288–289° C. MS (ESI, pos. ion) m/z: 570 (M+1).

Provenance & Evidence