JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
1827
114.5, 113.2, 101.1, 98.7, 96.2, 95.2, 55.5, 55.2, 55.1, 48.9, 46.1;
1H-NMR (600 MHz, CDCl3) d 8.68 (s, 1H), 7.60–7.62 (m, 2H), 7.15
IR(neat): 2934, 2837, 1593, 1568, 1536, 1518, 1483, 1452, 1418, (d, J ¼ 3.6 Hz, 1H), 7.10 (s, 1H), 7.01–7.03 (m, 2H), 6.98 (s, 1H), 6.76
1248, 1209, 1161, 1032, 1003, 831, 734, 699 cmꢁ1; HRMS (ESI): m/z (s, 1H), 6.53 (d, J ¼ 3.7 Hz, 1H), 6.13 (t, J ¼ 2.0 Hz, 1H), 3.86 (s, 3H),
calcd for C25H28N6O2 [M þ H]þ 445.2347 found 445.2345.
3.84–3.77 (1H), 3.68 (s, 3H), 3.55–3.45 (1H), 2.63–2.66 (m, 5H), 2.32
(s, 1H), 2.06 (d, J ¼ 12.5 Hz, 1H), 1.81 (s, 5H), 1.72 (d, J ¼ 6.7 Hz, 2H),
1.59–1.67 (m, 1H); 13C-NMR (150 MHz, CDCl3) d 161.14, 158.38,
N-(3-Methoxy-5-((4-methylpiperazin-1-yl)methyl)phenyl)-7–(4-
methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (26)
156.44, 151.92, 151.00, 142.05, 131.07, 126.39, 125.83, 125.54,
114.61, 113.36, 101.17, 99.54, 97.05, 95.19, 60.95, 55.60, 55.36,
55.26, 51.66, 51.53, 49.90, 24.02, 23.33; IR(neat): 2937, 1594, 1567,
1537, 1519, 1484, 1461, 1418, 1356, 1249, 1207, 1162, 1030,
Following the procedure for 25, 24 and 7 provided the title com-
pound 26 (51%).
832, 735 cmꢁ1
.
1H-NMR (300 MHz, CDCl3) d 8.69 (s, 1H), 7.59 (d, J ¼ 9 Hz, 2H),
7.25 (s, 1H), 7.14 (d, J ¼ 3.6 Hz, 1H), 7. 02 (d, J ¼ 9 Hz, 2H), 6.99 (t,
J ¼ 2.1 Hz, 1H), 6.80 (t, J ¼ 2.1 Hz, 1H), 6.54 (d, J ¼ 3.6 Hz, 1H), 6.11
(t, J ¼ 2.1 Hz, 1H), 3.88 (s, 3H), 3.70 (s, 3H), 3.10 (t, J ¼ 5.1 Hz, 4H)
2.49 (t, J ¼ 5.1 Hz, 4H), 2.34 (s, 3H); 13C-NMR (150 MHz, CDCl3) d
160.9, 158.2, 156.2, 152.8, 151.7, 151.0, 142.0, 130.9, 126.5, 125.7,
114.5, 113.2, 101.1, 98.7, 96.2, 95.2, 55.5, 55.2, 55.1, 48.9, 46.1;
IR(neat): 2934, 2836, 2800, 1599, 1569, 1537, 1518, 1456, 1417,
1349, 1248, 1209, 1160, 1064, 832, 734, 699 cmꢁ1. HRMS (ESI): m/z
calcd for C25H28N6O2 [M þ H]þ 445.2347 found 445.2345.
N-(3-Methoxy-5–(4-(oxetan-3-yl)piperazin-1-yl)phenyl)-7–(4-
methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (30)
Following the procedure for 25, 20e and 7 provided the title
compound 30 (27%).
1H-NMR (600 MHz, CDCl3)
d 8.70 (s, 1H), 7.89–7.76 (0H),
7.76–7.65 (0H), 7.59 (d, J ¼ 8.7 Hz, 2H), 7.47–7.37 (0H), 7.34 (s, 1H),
7.25–7.19 (0H), 7.14 (d, J ¼ 3.4 Hz, 1H), 7.07 (s, 1H), 7.01 (d,
J ¼ 8.7 Hz, 2H), 6.82–6.77 (0H), 6.73 (s, 1H), 6.53 (d, J ¼ 3.4 Hz, 1H),
6.10 (s, 1H), 4.66–4.71 (m, 4H), 3.88 (d, J ¼ 12.8 Hz, 3H), 3.71 (d,
J ¼ 12.8 Hz, 3H), 3.53 (q, J ¼ 6.3 Hz, 1H), 3.11 (s, 4H), 2.39 (d,
J ¼ 4.1 Hz, 4H); 13C-NMR (150 MHz, CDCl3) d 160.86, 158.19, 156.25,
152.75, 151.67, 150.99, 142.03, 130.90, 126.56, 125.77, 114.46,
113.15, 101.11, 98.73, 96.22, 95.21, 75.47, 59.25, 55.53, 55.18,
49.63, 48.66; IR(neat): 2951, 2877, 2834, 1592, 1569, 1538, 1519,
N-(3-Methoxy-5–(4-(pyrrolidin-1-yl)piperidin-1-yl)phenyl)-7–(4-
methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (27)
Following the procedure for 25, 20b and 7 provided the title
compound 27 (10%).
1H-NMR (300 MHz, CDCl3) d: 8.69 (s, 1H), 7.60 (d, J ¼ 9 Hz, 2H),
7.17 (s, 1H), 7.15 (d, J ¼ 3.6 Hz, 1H), 7.02 (d, J ¼ 9 Hz, 2H), 6.94 (t,
J ¼ 1.8 Hz, 1H), 6.81 (t, J ¼ 1.8 Hz, 1H), 6.54 (d, J ¼ 3.6 Hz, 1H), 6.12
(t, J ¼ 1.8 Hz, 1H), 3.88 (s, 3H), 3.70 (s, 3H), 3.60 (d, J ¼ 12.3 Hz, 2H),
2.80–2.89 (m, 4H), 2.62 (t, J ¼ 12.3 Hz, 2H), 1.94–2.12 (m, 1H),
1.66–2.02 (m, 8H); 13C-NMR (150 MHz, CDCl3) d 160.9, 158.3, 156.1,
152.1, 151.7, 150.9, 142.0, 131.0, 126.7, 125.6, 114.6, 113.2, 101.2,
99.4, 97.3, 95.9, 62.0, 55.9, 55.2, 50.2, 48.5, 27.5, 23.6; IR(neat):
2954, 1592, 1568, 1537, 1519, 1418, 1248, 1209, 1034, 1157, 831,
734 cmꢁ1. HRMS (ESI): m/z calcd for C29H34N6O2 [M þ H]þ 499.2816
found 499.2812.
1484, 1453, 1418, 1316, 1248, 1212, 1161, 1028 cmꢁ1
.
N-(3-Methoxy-5–(8-azaspiro[4.5]decan-8-yl)phenyl)-7–(4-
methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (31)
Following the procedure for 25, 20g and 7 provided the title
compound 31 (12%).
1H-NMR (600 MHz, CDCl3) d 8.69 (s, 1H), 7.60 (dd, J ¼ 6.8, 2.0 Hz,
2H), 7.19 (s, 1H), 7.14 (d, J ¼ 3.6 Hz, 1H), 7.01–7.02 (m, 2H), 6.92 (s,
1H), 6.82 (d, J ¼ 1.7 Hz, 1H), 6.53 (d, J ¼ 3.6 Hz, 1H), 6.14 (d,
J ¼ 2.0 Hz, 1H), 3.86 (s, 3H), 3.70 (s, 3H), 3.06 (t, J ¼ 5.6 Hz, 4H),
1.62–1.64 (m, 4H), 1.52 (t, J ¼ 5.6 Hz, 4H), 1.43 (t, J ¼ 7.1 Hz, 4H);
13C-NMR (150 MHz, CDCl3) d 160.86, 158.22, 156.31, 153.41, 151.75,
150.95, 141.83, 130.89, 126.44, 125.61, 114.44, 113.12, 101.09,
99.02, 96.44, 94.79, 55.48, 55.17, 47.21, 40.73, 37.67, 37.32, 24.34;
IR(neat): 2935, 1592, 1568, 1537, 1519, 1484, 1462, 1418, 1248,
N-(3-Methoxy-5–(4-methyl-4-(pyrrolidin-1-yl)piperidin-1-yl)
phenyl)-7–(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-
amine (28)
Following the procedure for 25, 20c and 7 provided the title com-
pound 28 (22%).
1H-NMR (600 MHz, CDCl3) d 8.70 (s, 1H), 7.61 (dd, J ¼ 6.9, 2.0 Hz,
2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.14 (d, J ¼ 3.6 Hz, 1H), 7.01 (dd,
J ¼ 6.9, 1.9 Hz, 2H), 6.90 (s, 1H), 6.84 (d, J ¼ 1.6 Hz, 1H), 6.52 (d,
J ¼ 3.6 Hz, 1H), 6.14 (t, J ¼ 2.0 Hz, 1H), 3.85 (s, 3H), 3.69 (s, 3H),
3.18–3.22 (m, 2H), 3.01–3.05 (m, 2H), 2.60 (s, 4H), 1.76–1.80 (m,
2H), 1.72 (d, J ¼ 5.9 Hz, 4H), 1.50–1.54 (m, 2H), 0.96 (s, 3H); 13C-
NMR (150 MHz, CDCl3) d 160.96, 158.27, 156.48, 153.26, 151.83,
151.06, 141.97, 131.00, 126.44, 125.64, 114.50, 113.17, 101.17,
98.75, 96.18, 94.59, 55.57, 55.24, 52.25, 45.23, 44.52, 36.24, 24.14,
16.50; IR(neat): 2958, 2835, 1603, 1569, 1536, 1519, 1484, 1458,
1210, 1160, 1137, 1033, 831, 734 cmꢁ1
.
N-(3-Methoxy-5–(1-oxa-8-azaspiro[4.5]decan-8-yl)phenyl)-7–(4-
methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (32)
Following the procedure for 25, 20h and 7 provided the title
compound 32 (31%).
1H-NMR (600 MHz, CDCl3) d 8.69 (s, 1H), 7.60 (d, J ¼ 8.6 Hz, 2H),
7.22 (s, 1H), 7.14 (d, J ¼ 3.6 Hz, 1H), 7.02 (d, J ¼ 8.6 Hz, 2H), 6.87 (d,
J ¼ 15.8 Hz, 2H), 6.53–6.53 (m, 1H), 6.14 (s, 1H), 3.86 (t, J ¼ 6.7 Hz,
5H), 3.69 (s, 3H), 3.13–3.23 (m, 4H), 1.92–1.97 (m, 2H), 1.64–1.71
(m, 7H); 13C-NMR (150 MHz, CDCl3) d 160.90, 158.23, 156.31,
152.87, 151.75, 150.97, 141.89, 130.89, 126.43, 125.61, 114.46,
113.15, 101.09, 99.20, 96.62, 94.93, 79.98, 66.70, 55.50, 55.17,
1419, 1349, 1248, 1211, 1156, 1071, 1034 cmꢁ1
.
N-(3-Methoxy-5–(3-(pyrrolidin-1-yl)piperidin-1-yl)phenyl)-7–(4-
methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (29)
Following the procedure for 25, 20d and 7 provided the title 47.07, 36.26, 36.08, 25.48; IR(neat): 2938, 1592, 1568, 1538, 1519,
compound 29 (11%).
1484, 1462, 1418, 1347, 1300, 1248, 1209, 1161, 1133, 1034 cmꢁ1
.