Triethylamine → HCID 54767997, compound

Participants

Reaction Conditions

Reaction Steps

2-Methane sulfonylamino-3-[1-(4-phenoxyphenyl)-1H-indol-3-yl]propionamide (39) was prepared as follows: MeSO2Cl (0.3 g, 2.6 mmol) was added to a solution of compound 33 (0.2 g, 0.5 mmol) prepared in Example 8 and triethylamine (0.5 mL) in CHCl3 (15 mL) at 0° C. The resulting mixture was shaken at 30° C. for 48 hours, and then washed with water (4 mL). The solvent was removed to give crude compound 38 (LC/MS: m/z=479.2 [M+H]+ (Calc: 478.2)), which was dissolved in NH3 (2 mL 28% aqueous and 4 mL 7N in MeOH), and heated to 120° C. for 2 hours under microwave. The reaction mixture was diluted with CHCl3 (45 mL), washed with water (10 mL), concentrated and purified by column (Silica gel, TCM/MeOH 10/1) to give compound 39 as a brown solid (60 mg, 30% in two steps): 1H-NMR (400 MHz, CDCl3) δ: 7.61-7.63 (m, 1H), 7.41-7.42 (m, 1H), 7.3-7.34 (m, 4H), 7.0-7.18 (m, 8H), 6.13 (br, 1H, NH), 5.57 (br, 1H, NH), 5.2 (d, 1H, 7.9 Hz), 4.19-4.25 (m, 1H), 3.32-3.37 (m, 1H), 3.19-3.25 (m, 1H), 2.54 (s, 3H); LC/MS: m/z=450.1 [M+H]+ (Calc: 449.5).

Provenance & Evidence