Diisopropylethylamine → 6-Methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid [1-(2-fluoro-4-methanesulfonylamino-5-methyl-phenyl)-ethyl]-amide

Participants

Reaction Conditions

Reaction Steps

In a 20 ml vial, N-[4-(1-amino-ethyl)-5-fluoro-2-methyl-phenyl]-methanesulfonamide (100 mg, 0.4 mmol), 6-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (100 mg, 0.49 mmol) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (380 mg, 1.0 mmol) were dissolved in N,N-dimethylformamide (8 mL). N,N-Diisopropylethylamine (400 uL, 2.0 mmol) was added while stirring. The reaction was heated for 1 hour at 50° C. After cooling the reaction to room temperature, saturated NaHCO3 solution (20 ml) was poured into the vial and extracted with DCM (3×30 ml). The combined organics was washed once with brine (40 ml), dried over NaSO4, filtered and concentrated. Purification by HPLC yielded a solid (63.1 mg, 30%). m/z=435.2 (M+1). 1H-NMR (400 MHz, DMSO-d6) δ 9.24 (s, 1H), 8.34 (t, 1H, J=7.60 Hz), 7.21 (d, 1H, J=8.67 Hz), 7.06 (d, 1H, J=11.56 Hz), 7.00-6.97 (m, 1H), 6.68-6.62 (m, 2H), 5.11-5.06 (m, 1H), 3.68 (s, 3H), 3.00 (d, 31-1, J=0.97 Hz), 2.77-2.68 (m, 4H), 2.57-2.51 (m, 1H), 2.25 (s, 3H), 1.95-1.88 (m, 1H), 1.70-1.54 (m, 1H), 1.33 (d, 3H, J=7.13 Hz).

Provenance & Evidence