Supplementary Materialsmolecules-25-02059-s001. (brs, 1H, NH), 7.34 (t, = 7.6 Hz, 2H, ArH), 7.27= 6.3 Hz, 2H, OCH2), 4.10 (q, = 6.4 Hz, 2H, NCH2), 1.92 (s, 3H, CH3), 1.26 (t, = 7.1 Hz, 3H, CH3). HRMS (ESI) calcd for C13H17NO2Na [M+Na]+: 242.1151, found: 242.1151. (3b). Colorless liquid 937174-76-0 (35.1 g, 98%). 1H-NMR (CDCl3) 8.65 (brs, 1H, NH), 7.30 (t, = 7.3 Hz, 2H, ArH), 7.24= 7.1 Hz, 2H, OCH2), 3.45= 7.6 Hz, 2H, PhCH2), 1.82 (s, 3H, CH3), 1.25 (t, = 7.1 Hz, 3H, CH3). HRMS (ESI) calcd for C14H19NO2Na 937174-76-0 [M+Na]+: 256.1308, found: 256.1307. (3c). Colorless liquid (29.0 g, 92%). 1H-NMR (DMSO-= 0.4 Hz, 1H, C=C-H), 4.06 (q, = 7.1 Hz, 2H, CH2), 2.01 (s, 3H, CH3), 1.20 (t, = 7.1 Hz, 3H, CH3). HRMS (ESI) calcd for C12H16NO2 [M+H]+: 206.1176, found: 206.1170. (3d). Colorless liquid (30.2 g, 94%). 1H-NMR (CDCl3) 8.80 (brs, 1H, NH), 7.35 (d, = 1.4 Hz, 1H, ArH), 6.31C6.30 (m, 1H, ArH), 6.19 (d, = 3.2 Hz, 1H, ArH), 4.52 (s, 1H, C=C-H), 4.37 (d, = 6.3 Hz, 2H, NCH2), 4.08 (q, = 7.1 Hz, 2H, OCH2), 1.99 (s, 3H, CH3), 1.24 (t, = 7.1 Hz, 3H, CH3). HRMS (ESI) calcd for C11H15NO3Na [M+Na]+: 232.0949, found: 232.0949. (3e). Colorless liquid (30.8 g, 95%). 1H-NMR (CDCl3) 8.63 (brs, 1H, NH), 4.39(3f). Colorless liquid (25.3 g, 96%). 1H-NMR (CDCl3) 8.50 (brs, 1H, NH), 4.39 (s, 1H, C=C-H), 4.10C4.06 (m, 2H, OCH2), 3.70C3.66 (m, 1H, CH), 1.94 (s, 3H, CH3), 1.26C1.23 (m, 3H, CH3), 1.21-1.20 (m, 6H, 2CH3). HRMS (ESI) calcd for C9H18NO2 [M+H]+: 172.1332, found: 172.1335. (3g). White solid (1.82 g, 95%). M.p. 53C54 C. 1H-NMR (CDCl3) 10.14 (brs, 1H, NH), 7.01 (d, Igf1r = 8.8 Hz, 2H, ArH), 6.84 (d, = 8.9 Hz, 2H, ArH), 4.64 (s, 1H, C=C-H), 4.16= 7.0 Hz, 2H, OCH2), 1.88 937174-76-0 (s, 3H, CH3), 1.41 (t, = 7.0 Hz, 3H, CH3), 1.28 (t, = 7.1 Hz, 3H, CH3). HRMS (ESI) calcd for C14H19NO3Na [M+Na]+: 272.1257, found: 272.1252. (3h). White solid (2.0 g, 90%). M.p. 79C81 C. 1H-NMR (CDCl3) 9.84 (brs, 1H, NH), 7.30= 7.7 Hz, 2H, ArH), 4.68 (brs, 1 H, C=C-H), 4.17 (q, = 7.1 Hz, 2 H, OCH2), 3.13= 7.1 Hz, 3H, CH3), 1.22 (d, = 6.9 Hz, 6H, 2CH3), 1.12 (d, = 6.8 Hz, 6H, 2CH3). HRMS (ESI) calcd for C18H27NO2Na [M+Na]+: 312.1934, found: 312.1933. (3i). White solid (1.45 g, 94%). M.p. 74C75 oC. 1H-NMR (CDCl3) 8.76 (d, = 9.4 Hz, 1H, NH), 4.53 (s, 1H, C=C-H), 4.09 (q, = 7.1 Hz, 2H, OCH2), 3.79= 7.1 Hz, 3H, CH3). HRMS (ESI) calcd for C9H17NO4Na [M+Na]+: 226.1050, found: 226.1044. (3j). 937174-76-0 White solid (1.96 g, 99%). M.p. 59~60 C. 1H-NMR (CDCl3) 8.89 (brs, 1H, NH), 7.37= 6.4 Hz, 2H, NCH2), 1.87 (s, 3H, CH3), 1.47 (s, 9H, 3CH3). HRMS (ESI) calcd for C15H21NO2Na [M+Na]+: 270.1465, found: 270.1461. (3k). Light crystals (1.65 g, 94%). M.p. 51C53 C. 1H-NMR (CDCl3) 8.59 (brs, 1H, NH), 4.43 (s, 1H, C=C-H), 3.74 (t, = 5.3 Hz, 2H, CH2), 3.37 (q, = 5.6 Hz, 2H, CH2), 1.92 (s, 3H, CH3), 1.46(s, 9H, 3CH3). HRMS (ESI) calcd for C10H19NO3 Na [M+Na]+: 224.1257, found: 224.1252. (3l). White colored crystals (1.96 g, 93%). 1H-NMR (CDCl3) 10.10 (brs, 1H, NH), 7.01 (d, 8.8 Hz, 2H, ArH), 6.83 (d, 8.8 Hz, 2H, ArH), 4.58 (s, 1H, C=C-H), 4.01 (q, 7.0 Hz, 2H, OCH2), 1.86 (s, 3H, CH3), 1.50 (s, 9H, 3CH3), 1.41 (t, 7.0 Hz, 3H, CH3). HRMS (ESI): calcd for C16H23NO3Na [M+Na]+: 300.1576; found: 300.1567. (3m). White colored crystals (1.63 g, 92%). 1H-NMR (CDCl3) 10.34 (brs, 1H, NH), 7.30 (t, 7.8 Hz, 2H, ArH), 7.13 (t, 7.4 Hz, 1H, ArH), 7.08 (d, 7.6 Hz, 2H, ArH), 4.62 (s, 1H, C=C-H), 1.50 (s, 9H, 3CH3). HRMS (ESI): calcd for C14H19NO2Na [M+Na]+: 256.1313, found: 256.1307. (3n). White colored crystals (1.21 g, 90%). M.p. 49C51 C. 1H-NMR (CDCl3) 12.47 (brs, 1H,.