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1.8 Hz, 1H), 6.55 (dd, J = 16.7, 9.4 Hz, 1H), 5.97 (dd, J = 9.5, 1.8 Hz, 1H), 5.84 (s, 2H), 4.21 (s, 2H), 3.79 (t,
J = 8.1 Hz, 2H), 1.16 (t, J = 8.2 Hz, 2H), 0.19 (s, 9H). 13C NMR (50 MHz, CDCl3)
168.8, 146.0, 142.7,
δ
141.4, 138.3, 137.7, 135.6, 134.9, 129.4, 128.2, 127.6, 127.4, 126.2, 125.8, 121.2, 118.2, 118.0, 115.9, 92.4, 84.8,
84.3, 73.0, 66.3, 38.0, 17.7, −1.5. TLC-MS (ESI) m/z: 555.1 [M + Na]+ HPLC tret = 9.71 min.
N-(3-(3-acrylamidophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)cyclopentanecarboxamide (12a): The preparation
was carried out following General Procedure B starting from 70 mg 34a (0.14 mmol) in 5 mL DCM and
2 mL TFA. Flash purification (DCM/MeOH (2–8%)) afforded 40 mg (77%) of the final compound as a
1
white solid. H NMR (200 MHz, DMSO)
δ 11.84 (br s, 1H), 10.24 (s, 1H), 9.97 (s, 1H), 8.62–8.47 (m, 1H),
8.47–8.32 (m, 1H), 7.93 (s, 1H), 7.75 (d, J = 2.2 Hz, 1H), 7.68–7.54 (m, 1H), 7.49–7.26 (m, 2H), 6.49 (dd,
J = 16.9, 9.9 Hz, 1H), 6.28 (dd, J = 16.9, 1.6 Hz, 1H), 5.78 (dd, J = 9.9, 1.6 Hz, 1H), 2.91–2.71 (m, 1H),
1.99–1.46 (m, 8H). 13C NMR (50 MHz, DMSO)
126.9, 124.4, 121.7, 118.3, 117.3, 117.0, 116.7, 114.3, 45.1, 30.2, 25.8. TLC-MS (ESI) m/z: 397.0 [M + Na
δ
174.5, 163.3, 145.7, 139.5, 136.8, 135.6, 132.0, 129.7, 129.3,
+
]
HPLC tret = 7.38 min.
N-(3-(3-acrylamidophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)thiophene-2-carboxamide (12c): The preparation
was carried out following General Procedure B starting from 46 mg 34c (0.09 mmol) in 4.2 mL DCM and
1.8 mL TFA. Flash purification (DCM/MeOH (4–10%)) afforded 15 mg (44%) of the final compound as a
1
white solid. H NMR (200 MHz, DMSO-d6)
δ 11.94 (s, 1H), 10.42 (s, 1H), 10.27 (s, 1H), 8.55 (s, 2H), 8.06
(d, J = 3.7 Hz, 1H), 7.97 (s, 1H), 7.87 (d, J = 5.1 Hz, 1H), 7.82 (s, 1H), 7.65 (dd, J = 5.8, 2.1 Hz, 1H), 7.41 (s,
1H), 7.39 (s, 1H), 7.25 (t, J = 4.4 Hz, 1H), 6.49 (dd, J = 16.9, 9.8 Hz, 1H), 6.27 (dd, J = 17.0, 1.8 Hz, 1H),
5.77 (dd, J = 9.8, 2.2 Hz, 1H). 13C NMR (50 MHz, DMSO-d6)
δ 163.2, 160.1, 146.2, 139.9, 139.5, 138.0,
135.4, 131.9, 131.7, 129.3, 129.0, 128.7, 128.1, 126.9, 124.6, 121.6, 120.2, 117.2, 116.9, 116.7, 114.3. TLC-MS
(ESI) m/z: 411.3 [M + Na]+. HRMS ESI-TOF [M + H]+ m/z calcd. for C21H16N4O2S: 389.1067, found:
389.1072. HPLC tret = 6.44 min.
N-(3-(3-acrylamidophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)furan-2-carboxamide (12d): The preparation was
carried out following General Procedure B starting from 58 mg 34d (0.12 mmol) in 4.2 mL DCM and
1.8 mL TFA. Flash purification (DCM/MeOH (4–10%)) afforded 23 mg (54%) of the final compound as a
1
white solid. H NMR (200 MHz, DMSO-d6)
δ 11.92 (s, 1H), 10.34 (s, 1H), 10.22 (s, 1H), 8.57 (s, 2H), 7.96
(s, 2H), 7.86–7.74 (m, 1H), 7.62 (d, J = 5.3 Hz, 1H), 7.50–7.33 (m, 2H), 7.33 (d, J = 3.5 Hz, 1H), 6.72 (dd,
J = 3.2, 1.4 Hz, 1H), 6.48 (dd, J = 17.0, 9.8 Hz, 1H), 6.29 (dd, 1H), 5.77 (dd, J = 9.6, 2.0 Hz, 1H). 13C NMR
(50 MHz, DMSO-d6)
δ 163.2, 156.5, 147.6, 146.2, 145.6, 139.5, 138.0, 135.4, 131.9, 129.3, 128.4, 126.9, 124.5,
121.6, 120.2, 117.2, 116.9, 116.7, 114.6, 114.2, 112.1. TLC-MS (ESI) m/z: 395.2 [M + Na]+. HRMS ESI-TOF
[M + H]+ m/z calcd. for C21H16N4O3: 373.1295, found: 373.1300. HPLC tret = 5.88 min
N-(3-(3-acrylamidophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (12e): The preparation was carried out
following General Procedure B starting from 47 mg 34e (0.09 mmol) in 4.2 mL DCM and 1.8 mL TFA.
Flash purification (DCM/MeOH (4–10%)) afforded 10 mg (29%) of the final compound as a white solid.
1H NMR (400 MHz, DMSO-d6)
δ 11.92 (d, 1H), 10.39 (s, 1H), 10.23 (s, 1H), 8.62 (d, J = 2.3 Hz, 1H), 8.59
(d, J = 2.2 Hz, 1H), 8.03 (s, 1H), 8.01 (d, J = 1.6 Hz, 1H), 7.96 (s, 1H), 7.81 (d, J = 2.6 Hz, 1H), 7.66–7.61
(m, 1H), 7.60 (d, J = 6.7 Hz, 1H), 7.55 (t, J = 7.2 Hz, 2H), 7.41 (d, J = 6.5 Hz, 2H), 6.47 (dd, J = 16.9, 10.1
Hz, 1H), 6.27 (dd, J = 17.0, 2.1 Hz, 1H), 5.76 (dd, J = 10.0, 2.1 Hz, 1H). 13C NMR (101 MHz, DMSO-d6)
δ
165.5, 163.2, 146.1, 139.5, 138.0, 135.4, 134.6, 131.9, 131.5, 129.2, 129.1, 128.3, 127.5, 126.7, 124.4, 121.6,
120.0, 117.2, 116.9, 116.6, 114.3. TLC-MS (ESI) m/z: 405.3 [M + Na]+. HRMS ESI-TOF [M + H]+ m/z
calcd. for C23H18N4O2: 383.1503, found: 383.1509. HPLC tret = 6.74 min.
N-(3-(5-acetamido-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)acrylamide (12f): The preparation was carried out
following General Procedure B starting from 90 mg 34f (0.20 mmol) in 4.2 mL DCM and 1.8 mL TFA.
Flash purification (DCM/MeOH (10–16%)) afforded 26 mg (41%) of the final compound as a white
1
solid. H NMR (200 MHz, DMSO-d6)
δ
11.85 (s, 1H), 10.22 (s, 1H), 10.03 (s, 1H), 8.46 (s, 1H), 8.39 (s,
1H), 7.95 (s, 1H), 7.76 (s, 1H), 7.60 (d, J = 7.3 Hz, 1H), 7.38 (q, J = 7.7 Hz, 2H), 6.49 (dd, J = 16.9, 9.8 Hz,
1H), 6.28 (d, J = 16.5 Hz, 1H), 5.78 (d, J = 9.7 Hz, 1H), 2.08 (s, 3H). 13C NMR (50 MHz, DMSO-d6)
δ