Reactions were monitored by thin-layer chromatography (TLC) on precoated silica GF254 plates. High-resolution mass spectra (HRMS) were taken in ESI mode on Water Q-Tof. 1H-NMR and 13C-NMR spectra were generated on Bruker AM-400 and 500 spectrometers (Bruker Bioscience, Billerica, MA, USA) with TMS as the internal standard. All other chemicals were analytical grade and used without further purification.
3.1.3. General Procedure for Preparation of Compound 14a–14i
To a mixture of the intermediate 13 (1.2 mmol), substituted aniline (1.0 mmol), and DMF (8 mL), p-toluenesulfonic acid (PTSA, 4.0 mmol) was added. The mixture was stirred at 90 °C for 4 h under N2 atmosphere. The reaction solution was cooled to room temperature, then poured into ice water (100 mL), and the precipitate was filtered off, washed, and dried in a vacuum to obtain the crude product, which was purified by silica gel chromatography using a mixture of DCM/MeOH (100:1~30:1) to afford the product 14a–14i.
Compound 14a: White solid, yield: 34.0%. 1H NMR (500 MHz, DMSO-d6) δ 10.83 (s, 1H), 9.82 (s, 1H), 8.40 (d, J = 5.5 Hz, 1H), 8.23 (s, 1H), 7.70 (d, J = 8.6 Hz, 2H), 7.67–7.56 (m, 6H), 7.52 (t, J = 7.25Hz 1H), 7.45 (d, J = 7.7 Hz, 2H), 7.22 (d, J = 8.6 Hz, 2H), 6.48 (d, J = 5.5 Hz, 1H), 3.56 (s, 4H), 3.37 (s, 3H), 3.31 (s, 1H), 3.24 (q, J = 5.7 Hz, 2H), 2.73 (s, 3H), 2.34 (s, 5H), 1.65 (s, 2H). 13C NMR (126 MHz, DMSO-d6) δ 170.07, 166.25, 163.53, 161.69, 160.39, 159.90, 154.30, 147.98, 143.26, 136.81, 133.52, 129.95, 129.33, 128.05, 127.61, 122.80, 120.71, 118.06, 99.40, 97.61, 66.64, 56.59, 53.78, 33.79, 26.44, 11.95. HRMS: m/z C36H38N8O5 [M + Na]+ 685.2965, found 685.2866.
Compound 14b: White solid, yield: 12.0%. 1H NMR (500 MHz, DMSO-d6) δ 10.81 (s, 1H), 9.53 (s, 1H), 8.32 (d, J = 5.6 Hz, 1H), 7.69 (d, J = 8.9 Hz, 2H), 7.60 (t, J = 7.7 Hz, 2H), 7.54–7.49 (m, 4H), 7.46–7.43 (m, 2H), 7.37 (d, J = 8.7 Hz, 2H), 7.20 (d, J = 8.9 Hz, 2H), 6.37 (d, J = 5.6 Hz, 1H), 3.37 (s, 3H), 3.08 (s, 2H), 2.72 (s, 3H), 2.53 (s, 4H), 2.50 (s, 2H), 2.26 (s, 3H), 1.24 (s, 2H). 13C NMR (126 MHz, DMSO-d6) δ 170.00, 168.13, 163.53, 161.65, 160.31, 160.18, 154.32, 148.02, 136.71, 136.38, 133.51, 133.00, 129.95, 129.31, 127.56, 122.76, 120.63, 120.24, 119.55, 98.43, 97.63, 62.12, 54.94, 53.05, 46.09, 33.80, 11.95. HRMS: m/z C35H37N9O4 [M + Na]+ 670.2969, found 670.2864.
Compound 14c: White solid, yield: 32.0%. 1H NMR (500 MHz, DMSO-d6) δ 10.84 (s, 1H), 9.93 (s, 1H), 9.50 (s, 1H), 8.30 (d, J = 5.6 Hz, 1H), 7.71–7.66 (m, 4H), 7.62–7.56 (m, 3H), 7.54–7.49 (m, 3H), 7.47–7.43 (m, 2H), 7.38 (d, J = 8.4 Hz, 2H), 7.17 (d, J = 8.9 Hz, 2H), 6.82 (d, J = 8.8 Hz, 2H), 6.38 (d, J = 5.6 Hz, 1H), 3.37 (s, 3H), 2.74 (s, 3H). 13C NMR (126 MHz, DMSO-d6) δ 170.00, 163.60, 161.69, 160.27, 159.97, 154.32, 147.93, 139.97, 137.54, 136.79, 133.54, 133.14, 131.34, 129.96, 129.56, 129.32, 127.59, 127.18, 122.82, 122.09, 120.51, 119.75, 98.60, 97.66, 33.79, 11.97, 11.93. HRMS: m/z C34H29N7O5S [M + Na]+ 670.1951, found 670.1851.
Compound 14d: White solid, yield: 19.0%. 1H NMR (500 MHz, DMSO-d6) δ 10.81 (s, 1H), 9.53 (d, J = 19.7 Hz, 2H), 8.34 (d, J = 5.6 Hz, 1H), 7.73 (s, 1H), 7.67 (d, J = 8.8 Hz, 2H), 7.60 (t, J = 7.6 Hz, 2H), 7.52 (t, J = 7.4 Hz, 1H), 7.45 (d, J = 7.4 Hz, 2H), 7.30 (d, J = 7.8 Hz, 1H), 7.20 (d, J = 8.8 Hz, 3H), 7.03 (d, J = 8.1 Hz, 1H), 6.39 (d, J = 5.6 Hz, 1H), 3.37 (s, 4H), 3.10 (s, 2H), 2.72 (s, 3H), 2.54 (s, 3H), 2.41 (s, 4H), 2.20 (s, 3H). 13C NMR (126 MHz, DMSO-d6) δ 170.00, 168.46, 163.51, 161.64, 160.31, 160.23, 154.27, 147.98, 140.89, 138.88, 136.69, 133.50, 129.95, 129.33, 128.82, 127.60, 122.79, 120.64, 115.13, 113.59, 110.94, 98.75, 97.56, 62.05, 55.07, 53.06, 46.15, 33.79, 11.93. HRMS: m/z C35H37N9O4 [M + Na]+ 670.2969, found 670.2865.
Compound 14e: White solid, yield: 28.0%. 1H NMR (500 MHz, DMSO-d6) δ 10.81 (s, 1H), 9.67 (s, 1H), 8.36 (d, J = 5.5 Hz, 1H), 8.33 (s, 1H), 7.96 (s, 1H), 7.73 (d, J = 7.7 Hz, 1H), 7.68 (d, J = 8.7 Hz, 2H), 7.60 (t, J = 7.5 Hz, 2H), 7.52 (t, J = 7.1 Hz, 1H), 7.45 (d, J = 7.5 Hz, 2H), 7.30 (d, J = 7.4 Hz, 1H), 7.20 (d, J = 8.6 Hz, 2H), 7.16 (t, J = 7.7 Hz, 1H), 6.42 (d, J = 5.5 Hz, 1H), 3.56 (s, 4H), 3.37 (s, 3H), 3.25 (dd, J = 6.6 Hz, J = 12.2Hz, 2H), 2.73 (s, 3H), 2.35 (s, 6H), 1.67 (s, 2H). 13C NMR (126 MHz, DMSO-d6) δ 170.05, 166.93, 163.53, 161.65, 160.38, 160.16, 154.31, 147.98, 140.69, 136.73, 135.79, 133.51, 129.95, 129.32, 128.45, 127.58, 122.80, 121.91, 120.74, 120.31, 118.89, 98.96, 97.58, 66.59, 56.52, 38.21, 33.80, 31.62, 30.30, 11.94. HRMS: m/z C36H38N8O5 [M + Na]+ 685.3000, found 685.2864.
Compound 14f: White solid, yield: 84.0%. 1H NMR (500 MHz, DMSO-d6) δ 10.82 (s, 1H), 9.46 (s, 1H), 8.32 (d, J = 5.5 Hz, 1H), 7.69 (d, J = 8.6 Hz, 2H), 7.60 (t, J = 7.5 Hz, 2H), 7.52 (t, J = 7.3 Hz, 1H), 7.44 (d, J = 7.3 Hz, 4H), 7.30 (d, J = 4.0 Hz, 4H), 7.19 (d, J = 8.4 Hz, 3H), 6.95 (d, J = 7.8 Hz, 2H), 6.38 (d, J = 5.5 Hz, 1H), 5.18 (s, 1H), 4.48 (t, J = 5.5 Hz, 1H), 2.72 (s, 3H), 1.81 (dt, J = 14.3, 7.9 Hz, 2H). 13C NMR (126 MHz, DMSO-d6) δ 170.08, 163.54, 161.67, 160.29, 160.20, 154.34, 148.10, 146.65, 138.29, 136.71, 135.44, 133.51, 129.95, 129.30, 128.42, 127.56, 126.24, 122.91, 120.78, 119.44, 98.29, 97.61, 72.09, 33.79, 31.30, 11.94. HRMS: m/z C37H32N6O4 [M + Na]+ 647.2485, found 647.2393.
Compound 14g: White solid, yield: 9.0%. 1H NMR (400 MHz, DMSO-d6) δ 10.77 (s, 1H), 9.87 (d, J = 4.1 Hz, 2H), 8.40 (d, J = 5.6 Hz, 1H), 8.03 (s, 1H), 7.76 (s, 2H), 7.69 (d, J = 8.9 Hz, 2H), 7.60 (t, J = 7.6 Hz, 2H), 7.51 (t, J = 7.4 Hz, 1H), 7.43 (d, J = 7.4 Hz, 2H), 7.21 (d, J = 8.9 Hz, 2H), 6.50 (d, J = 5.6 Hz, 1H), 3.36 (s, 3H), 3.11 (s, 2H), 2.71 (s, 3H), 2.54 (s, 2H), 2.41 (s, 4H), 2.15 (s, 3H), 1.35–1.20 (m, 2H). 13C NMR (126 MHz, DMSO-d6) δ 170.07, 169.06, 163.52, 161.63, 160.40, 159.75, 154.44, 147.82, 137.66, 136.92, 134.24, 133.55, 129.94, 129.24, 127.45, 124.52, 123.71, 122.64, 121.54, 120.87, 117.08, 99.63,97.71, 61.51, 54.91, 53.11, 46.03, 33.82, 11.94. HRMS: m/z C36H36N10O4 [M + Na]+ 695.2921, found 695.2819.
Compound 14h: White solid, yield: 29.1%. 1H NMR (500 MHz, DMSO-d6) δ 10.81 (s, 1H), 9.76 (s, 1H), 9.34 (s, 1H), 8.38 (d, J = 5.6 Hz, 1H), 7.70 (d, J = 8.8 Hz, 2H), 7.65 (d, J = 9.0 Hz, 1H), 7.60 (t, J = 7.6 Hz, 3H), 7.53 (d, J = 7.4 Hz, 1H), 7.44 (d, J = 7.4 Hz, 2H), 7.21 (d, J = 8.8 Hz, 3H), 6.48 (d, J = 5.6 Hz, 1H), 3.37 (s, 3H), 3.08 (s, 2H), 2.72 (s, 3H), 2.51 (s, 2H), 2.50 (s, 2H), 2.34 (s, 4H), 2.14 (s, 3H). 13C NMR (126 MHz, DMSO-d6) δ 170.05, 168.52, 163.51, 161.61, 159.81, 154.33, 147.90, 136.89, 133.50, 129.29, 127.50, 123.71, 122.77, 120.68, 119.37, 114.56, 106.09, 61.53, 55.14, 53.07, 46.10, 33.80, 11.95. HRMS: m/z C35H36FN9O4Na [M + Na]+ 688.2921, found 688.2776.
Compound 14i: White solid, yield: 39.1%. 1H NMR (500 MHz, DMSO-d6) δ 10.81 (s, 1H), 9.72 (s, 1H), 8.36 (d, J = 5.5 Hz, 1H), 7.68 (d, J = 8.8 Hz, 2H), 7.60 (t, J = 7.6 Hz, 2H), 7.55–7.48 (m, 3H), 7.45 (d, J = 7.5 Hz, 2H), 7.20 (d, J = 8.7 Hz, 2H), 7.03 (d, J = 7.9 Hz, 2H), 6.48 (d, J = 5.2 Hz, 1H), 3.38 (s, 3H), 3.05 (s, 3H), 2.78 (s, 2H), 2.72 (s, 3H), 2.24 (d, J = 34.2 Hz, 8H), 2.09 (s, 3H). 13C NMR (126 MHz, DMSO-d6) δ 170.19, 169.12, 163.53, 161.70, 160.43, 159.91, 154.40, 148.14, 139.78, 137.07, 136.76, 133.52, 129.94, 129.29, 127.57, 127.49, 123.07, 120.94, 119.78, 98.83, 59.19, 55.05, 52.76, 33.81, 11.92. HRMS: m/z C36H40N9O4 [M + H]+ 662.3125, found 662.3206.
3.1.6. General Procedure for Preparation of the Title Compounds 18a–18o
To a mixture of the intermediate 17 (1.2 mmol), substituted aniline (1.0 mmol), and DMF (8 mL), p-toluenesulfonic acid (PTSA, 4.0 mmol) was added. The mixture was stirred at 90 °C for 4 h under N2 atmosphere. The reaction solution was cooled to room temperature, then poured into ice water (100 mL), and the precipitate was filtered off, washed, and dried in a vacuum to obtain the crude product, which was purified by silica gel chromatography using a mixture of DCM/MeOH (100:1~40:1) to afford the product 18a–18o.
Compound 18a: White solid, yield: 36.6%. 1H NMR (500 MHz, DMSO-d6) δ 10.16 (s, 1H), 10.09 (s, 1H), 9.36 (s, 1H), 8.28 (d, J = 5.6 Hz, 1H), 7.70 (d, J = 8.9 Hz, 2H), 7.66 (dd, J = 9.0, 5.1 Hz, 2H), 7.35 (d, J = 4.4 Hz, 2H), 7.20–7.12 (m, 4H), 6.75 (d, J = 8.3 Hz, 2H), 6.35 (d, J = 5.6 Hz, 1H), 3.55 (t, J = 4.7 Hz, 2H), 3.51 (t, J = 4.5 Hz, 2H), 3.01 (t, J = 4.6 Hz, 2H), 2.94 (t, J = 4.7 Hz, 2H), 2.01 (s, 3H), 1.51 (d, J = 8.5 Hz, 4H). 13C NMR (126 MHz, DMSO-d6) δ 170.10, 168.74 (d, J = 3.86 Hz, 1C), 168.60, 160.21 (d, J = 13.67 Hz, 1C), 159.72, 157.81, 148.68, 146.16, 136.58, 135.62 (d, J = 1.50 Hz, 1C), 133.34, 122.88 (d, J = 7.75 Hz, 1C), 122.50 (d, J = 17.70 Hz, 1C), 120.43, 116.79, 115.62, 115.45, 97.77, 50.01, 49.64, 45.99, 31.80, 21.60, 16.00. HRMS: m/z C33H32FN7O4 [M + H]+ 610.2500, found 610.2537.
Compound 18b: White solid, yield: 13.5%. 1H NMR (500 MHz, DMSO-d6) δ 10.21 (s, 1H), 10.06 (s, 1H), 9.94 (s, 1H), 9.47 (s, 1H), 8.30 (d, J = 5.6 Hz, 1H), 7.70 (t, J = 9.6 Hz, 4H), 7.65 (dd, J = 8.9, 5.1 Hz, 2H), 7.59 (t, J = 7.4 Hz, 1H), 7.53 (t, J = 7.7 Hz, 2H), 7.41 (d, J = 8.3 Hz, 2H), 7.19–7.13 (m, 4H), 6.85 (d, J = 8.7 Hz, 2H), 6.36 (d, J = 5.6 Hz, 1H), 1.52 (d, J = 4.8 Hz, 4H). 13C NMR (126 MHz, DMSO-d6) δ 170.04, 168.69, 168.15, 160.32, 160.15, 159.70, 157.79, 148.52, 136.73, 136.39, 135.65 (d, J = 1.54 Hz, 1C), 132.93, 122.85 (d, J = 7.72 Hz, 1C), 122.35, 122.14, 120.31, 119.54, 115.60, 115.42, 98.37, 62.07, 54.85, 52.96, 45.95, 31.93, 15.98. HRMS: m/z C33H27FN6O5S [M + H]+ 639.1748, found 639.1833.
Compound 18c: White solid, yield: 3.4%. 1H NMR (500 MHz, DMSO-d6) δ 10.15 (s, 1H), 10.10 (s, 1H), 9.49 (s, 2H), 8.32 (d, J = 5.6 Hz, 1H), 7.72 (d, J = 8.9 Hz, 2H), 7.65 (dd, J = 9.0, 5.1 Hz, 2H), 7.47 (d, J = 8.1 Hz, 2H), 7.38 (d, J = 8.8 Hz, 2H), 7.21–7.13 (m, 4H), 6.37 (d, J = 5.6 Hz, 1H), 3.05 (s, 2H), 2.51 (s, 4H), 2.42 (s, 4H), 2.20 (s, 3H), 1.51 (d, J = 10.8 Hz, 4H). 13C NMR (126 MHz, DMSO-d6) δ 169.99, 168.83, 168.65, 160.28, 160.03, 159.72, 157.81, 148.43, 139.99, 137.55, 136.77, 135.58 (d, J = 2.49 Hz, 1C), 133.15, 131.39, 129.57, 127.17, 122.94 (d, J = 7.88 Hz, 1C), 122.32, 122.08 (d, J = 10.53 Hz, 1C), 119.88, 115.60, 115.43, 98.61, 31.84, 16.02. HRMS: m/z C34H35FN8O4 [M + H]+ 639.2765, found 639.2849.
Compound 18d: White solid, yield: 42.0%. 1H NMR (500 MHz, DMSO-d6) δ 10.16 (s, 1H), 10.09 (s, 1H), 9.83 (s, 1H), 8.40 (d, J = 5.6 Hz, 1H), 8.21 (t, J = 5.4 Hz, 1H), 7.72 (d, J = 8.9 Hz, 2H), 7.69–7.59 (m, 6H), 7.21 (d, J = 8.9 Hz, 2H), 7.16 (t, J = 8.9 Hz, 2H), 6.48 (d, J = 5.6 Hz, 1H), 3.56 (t, J = 4.4 Hz, 4H), 3.25 (q, J = 6.7 Hz, 2H), 2.38–2.27 (m, 6H), 1.66 (t, J = 7.05 Hz, 2H), 1.51 (d, J = 10.35 Hz, 4H). 13C NMR (126 MHz, DMSO-d6) δ 170.08, 168.77, 168.67, 166.26, 160.42, 159.87, 157.79, 148.53, 143.23, 136.77, 135.65 (d, J = 2.56 Hz, 1C), 128.10, 127.66, 122.87 (d, J = 7.82 Hz, 1C), 122.40 (d, J = 4.23 Hz, 1C), 118.07, 115.59, 115.42, 99.32, 66.67, 56.60, 53.80, 38.17, 31.95, 26.54, 15.94. HRMS: m/z C35H36FN7O5 [M + H]+ 654.2762, found 654.2842.
Compound 18e: White solid, yield: 10.9%. 1H NMR (400 MHz, DMSO-d6) δ 10.07 (s, 1H), 10.00 (s, 1H), 9.02 (s, 1H), 8.16 (d, J = 5.6 Hz, 1H), 7.62 (d, J = 8.9 Hz, 2H), 7.57 (dd, J = 9.1, 5.1 Hz, 2H), 7.14 (d, J = 8.2 Hz, 2H), 7.10 (s, 2H), 7.09–7.07 (m, 2H), 6.36 (d, J = 8.5 Hz, 2H), 6.17 (d, J = 5.5 Hz, 1H), 3.36 (t, J = 5.6 Hz, 3H), 3.18 (s, 3H), 3.04 (t, J = 5.6 Hz, 2H), 1.43 (s, 4H). 13C NMR (101 MHz, DMSO-d6) δ 170.02, 168.79, 168.68, 160.45, 159.96, 157.58, 153.82, 148.64, 140.72, 136.55, 135.61 (d, J = 2.60 Hz, 1C), 122.90 (d, J = 7.91 Hz, 1C), 122.39, 122.21, 115.62, 115.40, 112.67, 97.24, 71.06, 58.45, 43.53, 32.01, 16.00. HRMS: m/z C30H29FN6O4 [M + H]+ 557.2234, found 557.2288.
Compound 18f: White solid, yield: 7.4%. 1H NMR (400 MHz, DMSO-d6) δ 10.15 (s, 1H), 10.08 (s, 1H), 9.45 (s, 1H), 8.31 (d, J = 5.6 Hz, 1H), 7.70 (d, J = 8.9 Hz, 2H), 7.65 (dd, J = 9.1, 5.1 Hz, 2H), 7.43 (d, J = 8.2 Hz, 2H), 7.31 (d, J = 4.3 Hz, 4H), 7.25–7.20 (m, 1H), 7.20–7.13 (m, 4H), 6.95 (d, J = 8.4 Hz, 2H), 6.36 (d, J = 5.6 Hz, 1H), 5.21 (s, 1H), 4.51–4.46 (m, 1H), 1.88–1.76 (m, 2H), 1.48 (d, J = 3.5 Hz, 4H). 13C NMR (101 MHz, DMSO-d6) δ 170.06, 168.68 (d, J = 3.29 Hz, 1C), 160.20, 159.94, 157.55, 148.56, 146.68, 138.30, 136.71, 135.66 (d, J = 2.58 Hz, 1C), 135.44, 128.47 (d, J = 4.96 Hz, 1C), 127.09, 126.26, 122.84 (d, J = 7.87 Hz, 1C), 122.41, 122.25, 119.39, 115.63, 115.41, 98.27, 72.17, 41.54, 31.90, 31.37, 15.97. HRMS: m/z C36H30FN5O4 [M + H]+ 618.2438, found 618.2617.
Compound 18g: White solid, yield: 30.3%. 1H NMR (400 MHz, DMSO-d6) δ 10.14 (s, 1H), 10.09 (s, 1H), 9.48 (s, 1H), 9.47 (s, 1H), 8.32 (d, J = 5.6 Hz, 1H), 7.71 (d, J = 8.9 Hz, 2H), 7.64 (dd, J = 9.0, 5.1 Hz, 2H), 7.47 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 8.8 Hz, 2H), 7.16 (q, J = 8.7 Hz, 4H), 6.36 (d, J = 5.6 Hz, 1H), 3.04 (s, 2H), 2.50–2.39 (m, 8H), 2.33 (q, J = 7.1 Hz, 2H), 1.51 (d, J = 8.5 Hz, 4H), 0.99 (t, J = 7.2 Hz, 3H). 13C NMR (101 MHz, DMSO-d6) δ 170.05, 168.72, 168.19, 160.15, 159.95, 157.57, 148.55, 136.71, 136.39, 135.63 (d, J = 2.59 Hz, 1C), 132.93, 122.87 (d, J = 7.87 Hz, 1C), 122.35, 122.17, 120.32, 119.55, 115.62, 115.40, 98.37, 62.21, 53.24, 52.62, 52.02, 31.87, 16.01, 12.40. HRMS: m/z C35H37FN8O4 [M + H]+ 653.2922, found 653.3003.
Compound 18h: White solid, yield: 13.4%. 1H NMR (400 MHz, DMSO-d6) δ 10.14 (s, 1H), 10.10 (s, 1H), 9.48 (s, 1H), 9.47 (s, 1H), 8.32 (d, J = 5.6 Hz, 1H), 7.71 (d, J = 8.9 Hz, 2H), 7.64 (dd, J = 9.0, 5.1 Hz, 2H), 7.47 (d, J = 8.7 Hz, 2H), 7.37 (d, J = 8.8 Hz, 2H), 7.16 (q, J = 8.6 Hz, 4H), 6.36 (d, J = 5.6 Hz, 1H), 3.04 (s, 2H), 2.67 (s, 1H), 2.55–2.50 (m, 8H), 1.50 (d, J = 8.4 Hz, 4H), 0.98 (d, J = 6.5 Hz, 6H). 13C NMR (101 MHz, DMSO-d6) δ 170.04, 168.72, 168.20, 160.15, 159.95, 157.56, 148.55, 136.71, 136.40, 135.63 (d, J = 2.58 Hz, 1C), 132.92, 122.87 (d, J = 8.04 Hz, 1C), 122.34, 122.17, 120.40, 119.55, 115.62, 115.40, 98.38, 78.93, 66.79, 62.19, 48.28, 31.88, 18.60, 16.00. HRMS: m/z C36H39FN8O4 [M + H]+ 667.3078, found 667.3160.
Compound 18i: White solid, yield: 15.7%. 1H NMR (400 MHz, DMSO-d6) δ 10.07 (s, 1H), 10.02 (s, 1H), 9.41 (s, 1H), 9.40 (s, 1H), 8.25 (d, J = 5.6 Hz, 1H), 7.64 (d, J = 8.9 Hz, 2H), 7.57 (dd, J = 9.1, 5.1 Hz, 2H), 7.39 (d, J = 8.6 Hz, 2H), 7.30 (d, J = 8.9 Hz, 2H), 7.09 (q, J = 8.8 Hz, 4H), 6.29 (d, J = 5.6 Hz, 1H), 2.97 (s, 2H), 2.4 (d, J = 1.7 Hz, 8H), 2.12 (d, J = 6.5 Hz, 2H), 1.43 (d, J = 8.8 Hz, 4H), 1.01 (t, J = 7.2 Hz, 1H), 0.41–0.35 (m, 2H), 0.01 (d, J = 4.8 Hz, 2H). 13C NMR (101 MHz, DMSO-d6) δ 170.05, 168.72, 168.20, 160.15, 159.95, 157.56, 148.55, 136.71, 136.39, 135.63 (d, J = 2.55 Hz, 1C), 132.92, 122.87 (d, J = 7.90 Hz, 1C), 122.35, 122.17, 120.33, 119.54, 115.62, 115.40, 98.37, 63.19, 62.24, 52.96, 46.16, 31.89, 16.01, 8.67, 4.19. HRMS: m/z C37H39FN8O4 [M + H]+ 679.3078, found 679.3158.
Compound 18j: White solid, yield: 34.8%. 1H NMR (400 MHz, DMSO-d6) δ 10.14 (s, 1H), 10.07 (s, 1H), 9.55 (s, 1H), 9.48 (s, 1H), 8.32 (d, J = 5.6 Hz, 1H), 7.71 (d, J = 8.9 Hz, 2H), 7.64 (dd, J = 9.1, 5.1 Hz, 2H), 7.47 (d, J = 8.7 Hz, 2H), 7.38 (d, J = 8.9 Hz, 2H), 7.20–7.12 (q, J = 8.8 Hz, 4H), 6.36 (d, J = 5.6 Hz, 1H), 3.51–3.44 (m, 4H), 3.10 (s, 2H), 2.49 (s, 2H), 2.44 (t, J = 4.8 Hz, 2H), 1.99 (s, 3H), 1.50 (d, J = 8.7 Hz, 4H). 13C NMR (101 MHz, DMSO-d6) δ 170.05, 168.72 (d, J = 5.70 Hz, 1C), 168.60, 168.05, 160.15, 159.96, 157.57, 148.54, 136.72, 136.43, 135.62 (d, J = 2.60 Hz, 1C), 132.93, 122.89 (d, J = 7.95 Hz, 1C), 122.36, 122.15, 120.42, 119.51, 115.63, 115.41, 98.36, 61.83, 53.33, 52.89, 46.04, 31.91, 21.62, 15.96. HRMS: m/z C35H35FN8O5 [M + H]+ 667.2714, found 667.2802.
Compound 18k: White solid, yield: 13.9%. 1H NMR (400 MHz, DMSO-d6) δ 10.17 (s, 1H), 10.07 (s, 1H), 9.95 (s, 1H), 9.89 (s, 1H), 8.46 (d, J = 5.6 Hz, 1H), 8.02 (s, 1H), 7.87–7.74 (m, 4H), 7.69 (dd, J = 9.1, 5.1 Hz, 2H), 7.26 (d, J = 8.9 Hz, 2H), 7.21 (t, J = 8.9 Hz, 2H), 6.57 (d, J = 5.6 Hz, 1H), 3.36 (s, 2H), 3.18 (s, 2H), 2.66–2.58 (m, 6H), 2.27 (s, 3H), 1.55 (d, J = 12.0 Hz, 4H). 13C NMR (101 MHz, DMSO-d6) δ 170.10, 169.06, 168.69, 168.59, 160.45, 159.69, 157.54, 148.24, 137.62, 136.97, 135.60 (d, J = 2.62 Hz, 1C), 134.30, 124.56, 123.65, 122.80 (d, J = 7.90 Hz, 1C), 122.23 (d, J = 8.48 Hz, 1C), 121.14, 116.98, 115.65, 115.42, 104.69, 99.52, 61.55, 54.90, 53.11, 45.99, 31.85, 15.99. HRMS: m/z C35H34FN9O4 [M + H]+ 664.2718, found 664.2795.
Compound 18l: White solid, yield: 10.9%. 1H NMR (400 MHz, DMSO-d6) δ 10.17 (s, 1H), 10.08 (s, 1H), 9.75 (s, 1H), 9.32 (s, 1H), 8.37 (d, J = 5.6 Hz, 1H), 7.73 (d, J = 8.9 Hz, 2H), 7.67–7.56 (m, 4H), 7.26 (d, J = 8.6 Hz, 1H), 7.21–7.13 (m, 4H), 6.45 (d, J = 5.6 Hz, 1H), 3.10 (s, 2H), 2.53 (s, 4H), 2.42 (s, 4H), 2.21 (s, 3H), 1.50 (s, 4H). 13C NMR (101 MHz, DMSO-d6) δ 170.06, 168.72, 168.65, 168.52, 160.36, 159.81, 157.55, 152.59, 148.37, 136.89, 135.62 (d, J = 2.55 Hz, 1C), 122.85 (d, J = 7.81 Hz, 1C), 122.32, 122.09, 119.43, 119.31, 115.63, 115.41, 114.62, 106.11, 99.15, 61.51, 55.01, 52.94, 45.93, 31.85, 16.02. HRMS: m/z C34H34F2N8O4 [M + H]+ 657.2671, found 657.2746.
Compound 18m: White solid, yield: 9.4%. 1H NMR (400 MHz, DMSO-d6) δ 10.20 (s, 1H), 10.06 (s, 1H), 9.71 (s, 1H), 8.36 (d, J = 5.6 Hz, 1H), 7.69 (d, J = 8.9 Hz, 2H), 7.64 (dd, J = 9.0, 5.1 Hz, 2H), 7.55 (d, J = 8.1 Hz, 2H), 7.21–7.13 (m, 4H), 7.05 (d, J = 8.3 Hz, 2H), 6.45 (d, J = 5.6 Hz, 1H), 3.06 (s, 3H), 2.80 (s, 2H), 2.30 (s, 8H), 2.13 (s, 3H), 1.48 (d, J = 9.2 Hz, 4H). 13C NMR (101 MHz, DMSO-d6) δ 170.12, 168.75, 168.66, 160.43, 159.96, 157.56, 148.55, 136.74, 136.28, 135.63, 127.56, 122.88 (d, J = 7.74 Hz, 1C), 122.54, 122.39, 121.49, 119.80, 115.64, 115.41, 98.97, 59.20, 54.96, 52.64, 46.00, 37.30, 31.80, 15.99. HRMS: m/z C35H37FN8O4 [M + H]+ 653.2922, found 653.3007.
Compound 18n: White solid, yield: 11.3%. 1H NMR (400 MHz, DMSO-d6) δ 10.20 (s, 1H), 10.13 (s, 1H), 9.59 (s, 1H), 9.53 (s, 1H), 8.38 (d, J = 5.6 Hz, 1H), 7.77 (d, J = 8.9 Hz, 2H), 7.69 (dd, J = 9.1, 5.1 Hz, 2H), 7.53 (d, J = 8.7 Hz, 2H), 7.43 (d, J = 8.9 Hz, 2H), 7.26–7.18 (m, 4H), 6.42 (d, J = 5.6 Hz, 1H), 3.54–3.46 (m, 1H), 3.23 (q, J = 6.8 Hz, 1H), 2.61 (s, 4H), 2.47 (s, 4H), 2.26 (s, 3H), 1.56 (d, J = 10.5 Hz, 4H), 1.20 (d, J = 6.8 Hz, 3H). 13C NMR (101 MHz, DMSO-d6) δ 171.15, 170.05, 168.71 (d, J = 4.87 Hz, 1C), 160.15, 159.94, 157.55, 148.52, 136.74, 136.31, 135.63 (d, J = 2.57 Hz, 1C), 133.10, 122.86 (d, J = 7.87 Hz, 1C), 122.35, 122.12, 120.20, 119.52, 115.62, 115.40, 98.36, 63.74, 56.50, 55.27, 45.96, 31.89, 16.00, 13.25. HRMS: m/z C35H37FN8O4 [M + H]+ 653.2922, found 653.3001.
Compound 18o: White solid, yield: 7.6%. 1H NMR (400 MHz, DMSO-d6) δ 10.20 (s, 1H), 10.13 (s, 1H), 9.61 (s, 1H), 9.57 (s, 1H), 8.37 (d, J = 5.6 Hz, 1H), 7.76 (s, 1H), 7.74 (d, J = 9.0 Hz, 2H), 7.70 (dd, J = 9.1, 5.1 Hz, 2H), 7.36 (d, J = 8.1 Hz, 1H), 7.27–7.17 (m, 5H), 7.09 (t, J = 8.1 Hz, 1H), 6.41 (d, J = 5.6 Hz, 1H), 3.18 (s, 2H), 2.62 (s, 6H), 2.56 (s, 2H), 2.34 (s, 3H), 1.52 (s, 4H). 13C NMR (101 MHz, DMSO-d6) δ 170.01, 168.65 (d, J = 6.48 Hz, 1C), 168.37, 160.27 (d, J = 6.39 Hz, 1C), 159.94, 157.55, 148.48, 140.90, 138.88, 136.71, 135.67 (d, J = 2.70 Hz, 1C), 128.95, 122.82 (d, J = 7.91 Hz, 1C), 122.31, 122.19, 115.63, 115.41, 113.65, 110.97, 98.72, 61.70, 54.63, 52.31, 45.38, 31.98, 15.87. HRMS: m/z C34H35FN8O4 [M + H]+ 639.2765, found 639.2827.