Material was purified applying as a yellow oil (15.4 mg, (50 toluene) CDCl3 )

Material was purified applying as a yellow oil (15.4 mg, (50 toluene) CDCl3 ) 7.22.14 (m, 4H), six.96.85 (m, 4H), a yellow oil (10.8 mg, 55 1 H NMR (400 MHz,affording 10-methyl-9,10-dihydroacridine 55 as3.89 (s, 2H), three.38 (s, ten ) 3H); 13 C NMR (101 MHz, CDCl3 ) 143.eight, 127.7,yellow 124.5, 120.7, 112.0, 33.four, 33.3 ATR-IR benzyl-N-methylaniline 56 as a 127.0, oil (15.4 mg, 14 ). max (neat)/cm-1 2922, 1635, 1595, 1494, 1460, 1367, 1178, 752; GC-MS [m/z ] (14.37 min): 55 1H NMR (400 MHz, CDCl3) 7.22 7.14 (m, 4H), 6.96 six.85 (m, 4H), three.89 (s, 2H 194 (100, [M-H]), 176 (42), 152 (14), 126 (4), 97 (9), 63 (10). Analytical information are in agreement (s, 3H); the literature MHz, with these reported in13C NMR (101[74]. CDCl3) 143.eight, 127.7, 127.0, 124.five, 120.7, 112.0, 33.four, 33.3 56 1 H NMR (400 max (neat)/cm-1 2922, 1635, 1595, 1494, 1460,(m, 2H), 7.16752; JGC-MS [m/z ] IR MHz, CDCl3 ) 7.32.26 (m, 2H), 7.24.18 1367, 1178, (d, = 7.three Hz, 2H), 7.05.00 (d, J = 7.1 Hz, 1H), six.77 (t, J = 7.4 Hz, 1H), six.65 (d, J = eight.1 Hz, 1H), three.87 (s, 2H), min): 194 (one hundred, [M-H]), 176 (42), 152 (14), 126 (four), 97 (9), 63 (ten). Analytical data three.53 (bs, 1H), 2.77 (s, 3H); 13 C NMR (101 MHz, CDCl3 ) 147.3, 139.four, 130.six, 128.eight, 128.six, agreement with these reported in max (neat)/cm-1 128.0, 126.five, 124.7, 117.1, 110.1, 38.0, 30.9; ATR-IRthe literature [74]. : 3431, 2893, 1604, 1512, 1307, 1161, 729. HRMS (ESI): calculated for3) 7.32 N 7.26 (m, ): 198.1277 7.18 (m,198.1277. (d, J = 7 56 1H NMR (400 MHz, CDCl C14 H16 ([MH] 2H), 7.24 found: 2H), 7.16 NMR information are2H), 7.05 7.00 (d, these reported within the(t, J = 7.4 Hz, 1H), 6.65 (d, J = 8.1 Hz, 1H), 3 in agreement with J = 7.1 Hz, 1H), six.77 literature [75].2H), 3.53 (bs, 1H), two.77 (s, 3H); 13C NMR (101 MHz, CDCl3) 147.3, 139.four, 130.six, 128.128.0, 126.five, 124.7, 117.1, 110.1, 38.0, 30.9; ATR-IR max (neat)/cm-1: 3431, 2893, 1604 NMR information are in agreement with these reported inside the literature [75].1307, 1161, 729. HRMS (ESI): calculated for C14H16N ([MH]): 198.1277 located:2H), 7.05 7.00 (d, J = 7.1 Hz, 1H), 6.77 (t, J = 7.four Hz, 1H), 6.65 (d, J = 8.1 Hz, 1H),2H), 3.53 (bs, 1H), 2.77 (s, 3H); 13C NMR (101 MHz, CDCl3) 147.three, 139.four, 130.6, 128.Molecules 2021, 26,128.0, 126.5, 124.7, 117.1, 110.1, 38.0, 30.9; ATR-IR max (neat)/cm-1: 3431, 2893, 1604 NMR data are in agreement with these reported within the literature [75].3.3.4. PF-06454589 Inhibitor Reaction 3.three.four. Reaction of N,2-dimethyl-N-phenylaniline 52 with KOtBu/MRTX-1719 site Et3SiH – neat: of N,2-dimethyl-N-phenylaniline 52 with KOtBu/Et3 SiH–Neat15 of discovered: 198 1307, 1161, 729. HRMS (ESI): calculated for C14H16N ([MH]): 198.1277Substrate 52 (99 mg, 1.0 equiv., (3.0 equiv., KOtBu (three.0 equiv., 1.five mmol, Substrate 52 (99 mg, 1.0 equiv., 0.five mmol), KOt Bu0.5 mmol), 1.five mmol, 168 mg), and Et3 SiH 168 mg (three.0 equiv., 1.5Et3SiH (three.0 ) had been sealed in 240 L) have been sealednitrogen-filled tube inside a nitrogen mmol, 240 equiv., 1.five mmol, a stress tube in a within a pressure glovebox. The contents of your pressure tube were stirred at 130 C for 18 h before the stress tube glovebox. The contents from the pressure tube have been stirred at 130 for 18 h befo was cooled to room temperature, opened to air and diluted with water (50 mL). The pressure extracted into Et2 room 50 mL). The combined organic phases organic products have been tube was cooled as well (3 emperature, opened to air and diluted with wa had been dried more than Na2 SO4 organic products had been extracted intomaterial was purified applying mL). The and concentrated in vacuo. The crude Et2O (three x 50 mL). T.