Molecules 2018, 23, 2002
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13C-NMR: δ 170.59, 168.12, 160.16, 142.37, 137.66, 132.74, 130.36, 129.35, 129.02, 128.23, 127.97, 127.58,
127.04, 126.54, 118.72, 103.22, 55.37, 37.50. ESI-MS (m/z) = 488.89 [M + H]+, HRMS(ESI) calcd. For
C26H22ClN4O4+: [M + H]+ m/z: 489.1324, found: 489.1311.
(S)-4-(2-(5-(3-Chloro-2-fluorophenyl)-1H-pyrazole-3-carboxamido)-3-phenylpropanamido)benzoic acid (7f):
◦
1
white solid product (258 mg, 84.8% yield), m.p.: 185–187 C, decomposition. H-NMR:
δ 13.86 (s, 1H,),
12.69 (s, 1H), 10.54 (s, 1H), 10.38 (s, 1H), 8.31–8.29 (d, J = 8.0 Hz, 1H), 7.91–7.86 (m, 2H), 7.73–7.67
(
(
m, 2H), 7.57 (s, 1H), 7.35–7.19 (m, 5H), 7.17–7.15 (m, 1H), 4.91–4.89 (m, 1H), 3.16–2.99 (m, 1H), 2.86–2.81
m, 1H). 13C-NMR:
δ 170.70, 168.35, 159.87, 155.44, 142.28, 137.77, 130.47, 129.42, 128.36, 128.00, 127.03,
126.68, 125.87, 121.01, 118.85, 106.21, 55.55, 37.46. ESI-MS (m/z) = 506.93 [M + H]+, HRMS(ESI) calcd.
For C26H21ClFN4O4+: [M + H]+ m/z: 507.1230, found: 507.1220.
(S)-4-(2-(5-(4-Chloro-2-fluorophenyl)-1H-pyrazole-3-carboxamido)-3-phenylpropanamido)benzoic acid (7g):
◦
white solid product (220 mg, 72.6% yield), m.p.: 143–145 C, decomposition. 1H-NMR:
δ
13.82
s, 1H), 12.70 (s, 1H), 10.55 (s, 1H), 9.00 (s, 1H), 7.94 (s, 1H), 7.90–7.88 (d, J = 8.4 Hz, 2H), 7.73–7.71
d, J = 8.4 Hz, 2H), 7.58–7.56 (m, 1H), 7.35–7.27 (m, 3H), 7.26–7.24 (m, 2H), 7.18–7.15 (m, 1H), 4.93–4.87
171.27, 167.62, 160.54, 158.03, 143.55, 138.26, 133.94, 131.04,
(
(
(m, 1H), 3.18–3.11 (m, 2H). 13C-NMR:
δ
129.91, 128.78, 127.11, 126.15, 125.80, 119.39, 117.65, 106.48, 55.92, 37.90. HRMS(ESI) calcd. For
C26H21ClFN4O4+: [M + H]+ m/z: 507.1230, found: 507.1215.
(S)-4-(2-(5-(5-Chloro-2-fluorophenyl)-1H-pyrazole-3-carboxamido)-3-phenylpropanamido)benzoic acid (7h):
1
grey solid product (176 mg, 57.9% yield), m.p.: 179–181 ◦C, decomposition. H-NMR:
δ
13.89–13.83
(m, 1H), 12.78 (s, 1H), 10.55 (s, 1H), 8.78–8.77 (m, 1H), 7.96–7.94 (m, 1H), 7.90–7.88 (d, J = 8.8 Hz,
2H), 7.71–7.69 (d, J = 8.4 Hz, 2H), 7.47–7.18 (m, 6H), 7.16–7.15 (m, 1H), 4.92–4.87 (m, 1H), 3.19–3.07
(
m, 2H). 13C-NMR):
δ 171.21, 168.05, 159.40, 143.20, 138.31, 130.98, 129.88, 129.5, 128.80, 127.73, 127.11,
119.32, 119.13, 118.89, 106.79, 55.95, 37.90. ESI-MS (m/z) = 506.87 [M + H]+, HRMS(ESI) calcd. For
C26H21ClFN4O4+: [M + H]+ m/z: 507.1230, found: 507.1221.
(S)-4-(2-(5-(2-Chloro-6-fluorophenyl)-1H-pyrazole-3-carboxamido)-3-phenylpropanamido)benzoic acid (7i):
1
white solid product (189 mg, 62.1% yield), m.p.: 203–205 ◦C, decomposition. H-NMR:
δ
13.74–13.70
(m, 1H), 10.64 (s, 1H), 7.89–7.87 (d, J = 8.8 Hz, 2H), 7.71–7.69 (d, J = 8.4 Hz, 2H), 7.54–7.42 (m, 2H),
7.38–7.36 (m, 3H), 7.28–7.24 (m, 2H), 7.19–7.15 (m, 1H), 7.08–6.98 (m, 1H), 4.92–4.86 (m, 1H), 3.21–3.09
(m, 2H). 13C-NMR:
δ 171.31, 168.49, 162.00, 143.11, 138.33, 134.48, 130.98, 129.94, 128.82, 127.69, 127.14,
126.53, 119.26, 115.63, 115.40, 108.35, 56.03, 37.88. ESI-MS (m/z) = 506.88 [M + H]+, HRMS(ESI) calcd.
For C26H21ClFN4O4+: [M + H]+ m/z: 507.1230, found: 507.1213.
(S)-4-(2-(5-(2,6-Difluorophenyl)-1H-pyrazole-3-carboxamido)-3-phenylpropanamido)benzoic acid (7j): white
◦
solid product (153 mg, 50.6% yield), m.p.: 205–207 C, decomposition. 1H-NMR:
δ
13.66 (s, 1H),
12.79–12.70 (m, 1H), 10.54 (s, 1H), 7.91–7.89 (d, J = 8.4 Hz, 2H), 7.73–7.70 (d, J = 8.4 Hz, 2H), 7.50 (s, 1H),
7.35–7.03 (m, 6H), 7.03–6.99 (m, 2H), 4.91–4.89 (m, 1H), 3.16–3.15 (m, 2H). 13C-NMR:
170.65, 166.99,
δ
160.63, 160.18, 158.08, 142.90, 137.62, 130.76, 130.46, 129.27, 128.20, 126.51, 125.53, 118.77, 112.31, 107.44,
55.16, 37.34. ESI-MS (m/z) = 490.98 [M + H]+, HRMS(ESI) calcd. For C26H21F2N4O4+: [M + H]+ m/z:
491.1525, found: 491.1500.
(S)-4-(2-(5-(3-Chloro-2,6-difluorophenyl)-1H-pyrazole-3-carboxamido)-3-phenylpropanamido)benzoicacid (7k):
1
white solid product (220 mg, 70.2% yield), m.p.: 129–131 ◦C, decomposition. H-NMR:
δ 13.80 (s, 1H),
12.74 (s, 1H), 10.53 (s, 1H), 7.91–7.89 (d, J = 8.4 Hz, 2H), 7.73–7.70 (m, 3H), 7.34–7.04 (m, 8H), 4.93–4.87
(m, 1H), 3.18–3.15 (m, 2H). 13C-NMR:
δ 171.23, 167.60, 157.27, 143.45, 138.22, 131.08, 129.86, 128.81,
127.13, 126.20, 119.39, 117.07, 113.99, 113.77, 108.30, 55.82, 37.94. ESI-MS (m/z) = 525.00 [M + H]+,
HRMS(ESI) calcd. For C26H20ClF2N4O4+: [M + H]+ m/z: 525.1136, found: 525.1116.
(S)-4-(2-(5-(4-Chloro-2,6-difluorophenyl)-1H-pyrazole-3-carboxamido)-3-phenylpropanamido)benzoic acid (7l):
1
white solid product (220 mg, 70.2% yield), m.p.: 123–125 ◦C, decomposition. H-NMR:
δ
13.93–13.77
(m, 1H), 12.78–12.72 (m, 1H), 10.59 (s, 1H), 9.04–9.02 (m, 1H), 7.91–7.89 (d, J = 8.8 Hz, 2 H), 7.73–7.71