Supplementary Materialsmolecules-20-15976-s001. individual window Plan 1 Synthesis of (4,6-dimethoxy-1,3,5-triazin-2-yl) amino acid

Supplementary Materialsmolecules-20-15976-s001. individual window Plan 1 Synthesis of (4,6-dimethoxy-1,3,5-triazin-2-yl) amino acid derivatives 3C9. In addition, (3). The product was obtained as a white powder, 6.81 g (83.4%) yield, mp 180C181 C; IR (KBr): 3500C2589 (br, OH, acid), 1709 (CO, acid) cm?1; 1H-NMR (400 MHz, DMSO-(4). The product was obtained as a white solid, 0.64 g (60.0%) yield; mp: 164C166 C; IR (KBr): 3574C2522 (br, OH, acid), 3255 (NH, amine), 1725 (CO, acid) cm?1; 1H-NMR (400 MHz, DMSO-= 5.9 BI-1356 supplier Hz, CH2), 8.13 (t, 1H, = 5.9 Hz, NCH); 13C-NMR (100 MHz, DMSO-(5). The product was BI-1356 supplier obtained as a white solid, 0.77 g (66.6%) yield; mp: 98C102 C; IR (KBr): 3557C2567 (br, OH, acid), 3372 (NH, amine), 1721 (CO, acid) cm?1; 1H-NMR (400 MHz, DMSO-= 7.3 Hz, CH3), 3.80 (s, 3H, OCCH3), 3.83 (s, 3H, OCCH3), 4.34 (quint, 1H, = 7.3 Hz, -CH), 8.20 (d, 1H, = 7.3 Hz, NCH), 11.18 (br s, 1H, COOH); 13C-NMR (100 MHz, DMSO-(6). The product was obtained as a white solid, 0.78 g (61.4%) yield; mp: 146C188 C; IR (KBr): 3570C2539 (br, OH, acid), 3259 (NH, amine), 1720 (CO, acid) cm?1; 1H-NMR (400 MHz, DMSO-= 6.6 Hz, CH3), 0.95 (d, 3H, = 6.6 Hz, CH3), 2.13 (octet, 1H, = MST1R 6.6 Hz, CH), 3.81 (s, 3H, OCCH3), 3.84 (s, 3H, OCCH3), 4.21 (t, 1H, = 6.6 Hz, -CH), 8.03 (d, 1H, = 7.3 Hz, NCH); 13C-NMR (100 MHz, DMSO-(7). The product was obtained as a white solid, 0.98 g (64.1%) yield; mp: 153C155 C; IR (KBr): 3431C2650 (br, OH, acid), 3256 (NH, amine), 1714 (CO, acid) cm?1; 1H-NMR (400 MHz, DMSO-= 13.9 Hz, 3= 10.2 Hz, CH2CPh), 3.14 (dd, 1H, 2= 13.9 Hz, 3= 3.7 Hz, CH2CPh), BI-1356 supplier 3.77 (s, 3H, OCH3), 3.80 (s, 3H, OCH3), 4.54C4.59 (m, 1H, -CH), 7.18C7.31 (m, 5H, ArCH), 8.20 (d, 1H, = 8.0 Hz, NCH); 13C-NMR (100 MHz, DMSO-(8). The product was obtained as a white solid, 0.91 g (67.4%) yield; mp: 102C103 C; IR (KBr): 3443C2551 (br, OH, acid), 3282 (NH, amine) 1725 (CO, acid) cm?1;1H-NMR (400 MHz, DMSO-= 5.9 Hz, CH3), 0.90 (d, 3H, = 6.6 Hz, CH3), 1.52 (m, 1H, CH), 1.68 (m, 2H, CH2), 3.80 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 4.35C4.38 (m, 1H, -CH), 8.16 (d, 1H, = 7.3 Hz, NCH); 13C-NMR (100 MHz, DMSO-(9). The product was obtained as a white solid, 0.98 g (72.5%) yield; mp: 118C119 C; IR (KBr): 3500C2536 (br, OH, acid), 3261 (NH, amine), 1715 (CO, acid) cm?1; 1H-NMR (400 MHz, DMSO-= 7.4 Hz, CH3CH2), 0.91 (d, 3H, = 6.6 Hz, CH3CH), 1.26C1.31 (m, 1H, CH2), 1.44C1.48 (m, 1H, CH2), 1.85C1.88 (m, 1H, CH), 3.81 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 4.27 (t, 1H, = 7.4 Hz, -CH), 8.04 (d, 1H, = 7.4 Hz, N(15). The product was obtained as a white solid, 0.44 g (79.1%) yield; mp: 128C130 C; IR (KBr): 3593C2853 (br, OH, acid), 1729 (CO, acid) cm?1; 1H-NMR (400 MHz, DMSO-(16). The product was obtained as a white solid, 0.51 g (79.0%) yield; mp: 211C214 C; IR (KBr): 3628C2664 (br, OH, acid), 3269 (NH, amine) 1676 (CO, acid) cm?1; 1H-NMR (400 MHz, DMSO-= 5.8 Hz, -CH2), 6.85 (t, 1H, = 5.8 Hz, NH), 12.37 (br s, 1H, COOH); 13C-NMR (100 MHz, DMSO-(17). The product was obtained as a white solid, 0.52 g (78.1%) yield; mp: 126C128 C; IR.