Aniline → HCID 59595044, compound

Participants

Reaction Steps

To a solution of 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylic acid prepared in Example 1, Part A (104 mg, 0.41 mmol) in NMP (1.8 mL) were added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (195 mg, 0.51 mmol) and N,N-diisopropylethylamine (0.22 mL, 1.26 mmol). After the resulting solution was stirred at RT for 2.3 h, a solution of the aniline prepared in Part B of Example 2 (84.3 mg, 0.465 mmol) in 1,2-dichloroethane (0.8 mL+0.4 mL rinse) was added. After heating at 80° C. with stirring for 16 h, the reaction was cooled to RT before being diluted first with water (30 mL) and then sat'd NaHCO3 (5.5 mL). Following extraction of the aqueous mixture (pH ˜9) with EtOAc (3×30 mL), the combined organic extracts were washed with water (20 mL), dried (Na2SO4) and evaporated. Chromatography (SiO2 230-400 mesh, 9/1 CH2Cl2/Ether) of the crude provided the desired amide (118.2 mg, 69% yield) as a yellow solid: MS (electrospray, + ions) m/z 417 (M+H).

Provenance & Evidence