Molecules 2018, 23, 1054
8 of 13
5
-(1-(2-Chlorophenyl)-2-methoxy-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl-2-((tert-butoxy-car
1
bonyl)amino)-3-phenylpropanoate (4e). Yellow oil. H-NMR (400 MHz, DMSO-d6):
δ 7.38 (t, 2H,
J = 6.4 Hz), 7.31–7.29 (m, 1H), 7.22–7.16 (m, 2H), 7.12–7.03 (m, 5H), 6.16 (s, 1H), 4.66 (s, 1H), 4.23–4.14
(
m, 1H), 3.47 (s, 3H), 3.35 (s, 2H), 3.26–3.10 (m, 2H), 2.92–2.80 (m, 2H), 2.67–2.57 (m, 2H), 1.16 (s, 9H).
+
ESI-MS (m/z) = 585.11 [M + H] .
5
-(1-(2-Chlorophenyl)-2-methoxy-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl-2-((tert-butoxy-car
1
bonyl)amino)-3-(1H-indol-2-yl)propanoate (4f). Yellow oil. H-NMR (400 MHz, DMSO-d ):
δ 10.86 (s,
6
1
H), 7.59 (d, 1H, J = 8.0 Hz), 7.53–7.48 (m, 3H), 7.39–7.33 (m, 2H), 7.18 (s, 1H), 7.06 (t, 1H, J = 8.0 Hz),
6
.98 (t, 1H, J = 8.0 Hz), 6.26 (s, 1H), 4.83 (s, 1H), 4.42–4.37 (m, 1H), 3.65 (s, 3H), 3.52 (s, 2H), 3.19–3.12
+
(m, 2H), 2.86–2.75 (m, 2H), 2.66–2.58 (m, 2H), 1.35 (s, 9H). ESI-MS (m/z) = 624.17 [M + H] .
1
-tert-Butyl 2-(5-(1-(2-chlorophenyl)-2-methoxy-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)
1
pyrrolidine-1,2-dicarboxylate (4g). Yellow oil. H-NMR (400 MHz, DMSO-d ):
δ 7.56 (t, 1H, J = 2.0 Hz
6
and 6.8 Hz), 7.46 (t, 1H, J = 13.6 Hz), 7.38–7.32 (m, 2H), 6.44 (s, 1H), 4.82 (s, 1H), 4.37–4.34 (m, 1H),
3
.63 (s, 3H), 3.52 (s, 2H), 3.41–3.27 (m, 2H), 2.80–2.74 (m, 2H), 2.66 (s, 2H), 2.33–2.26 (m, 1H), 1.98–1.94
+
(m, 1H), 1.86–1.80 (m, 2H), 1.35 (s, 9H). ESI-MS (m/z) = 535.05 [M + H] .
1
5
-tert-Butyl 2-(5-(1-(2-chlorophenyl)-2-methoxy-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)
-oxopyrrolidine-1,2-dicarboxylate (4h). Yellow oil. 1H-NMR (400 MHz, DMSO-d6):
δ
7.35 (dd, 1H,
J = 7.2 Hz), 7.28–7.25 (m, 1H), 7.17–7.14 (m, 2H), 6.30 (s, 1H), 4.66–4.62 (m, 2H), 3.43 (s, 3H), 3.22 (s, 2H),
+
2
.60–2.47 (m, 4H), 2.30–2.18 (m, 3H), 1.85–1.76 (m, 1H), 1.17 (s, 9H). ESI-MS (m/z) = 549.05 [M + H] .
5
-(2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl-2-((tert-butoxy-
1
carbonyl)amino)propanoate (4i). Yellow oil. H-NMR (400 MHz, DMSO-d ): 7.52–7.49 (m, 1H), 7.40–7.38
6
(
2
m, 2H), 7.27–7.22 (m, 2H), 6.43 (s, 1H), 4.78 (s, 1H), 4.08–4.06 (m, 1H), 3.48 (s, 2H), 2.89–2.72 (m, 4H),
.27–2.25 (m, 1H), 1.47–1.15 (m, 12H), 0.88–0.80 (m, 4H). ESI-MS (m/z) = 503.11 [M + H] .
+
5
-(2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl-2-((tert-butoxy-car
◦
1
bonyl)amino)-3-methylbutanoate (4j). White solid. m.p. 106–108 C. H-NMR (400 MHz, DMSO-d ):
6
δ
7.52–7.45 (m, 2H), 7.42–7.37 (m, 1H), 7.26–7.22 (m, 2H), 6.44 (s, 1H), 4.78 (s, 1H), 4.00 (t, 1H,
J = 6.4 Hz), 3.44 (t, 2H, J = 16.0 Hz), 2.80–2.69 (m, 4H), 2.38–2.36 (m, 1H), 2.11–2.06 (m, 1H), 1.38 (s, 9H),
+
+
+
0
.94–0.78 (m, 10H). ESI-MS (m/z) = 531.22 [M + H] , HRMS(ESI) calcd. for C H FN O S : [M + H]
28 36 2 5
m/z: 531.2323, found: 531.2314.
5
-(2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl-2-((tert-butoxy-
1
carbonyl)amino)-4-methylpentanoate (4k). Yellow oil. H-NMR (400 MHz, DMSO-d ): 7.52–7.48 (m, 2H),
6
7.40 (dd, 1H, J = 13.6 Hz), 7.26–7.21 (m, 2H), 6.43 (s, 1H), 4.78 (s, 1H), 4.17–4.12 (m, 1H), 3.44 (t, 2H,
J = 6.4 Hz), 2.80–2.70 (m, 4H), 2.37–2.35 (m, 1H), 1.66–1.42 (m, 3H), 1.37 (s, 9H), 0.90–0.80 (m, 10H).
+
ESI-MS (m/z) = 545.14 [M + H] .
5
-(2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl-2-((tert-butoxy-car
◦
1
bonyl)amino)-3-methylpentanoate (4l). White solid. m.p.: 80–82 C. H-NMR (400 MHz, DMSO-d ):
6
δ
7.52–7.45 (m, 2H), 7.40 (dd, 1H, J = 12.8 Hz), 7.26–7.21 (m, 2H), 6.43 (s, 1H), 4.77 (s, 1H), 4.05 (t, 1H,
J = 6.8 Hz), 3.44 (t, 2H, J = 15.2Hz), 2.80–2.69 (m, 4H), 2.39–2.35 (m, 1H), 1.86–1.82 (m, 1H), 1.38–1.20
+
+
(
[
m, 11H), 0.88–0.73 (m, 10H). ESI-MS (m/z) = 545.10 [M + H] , HRMS(ESI) calcd. for C H FN O S :
29 38 2 5
M + H] m/z: 545.2480, found: 545.2467.
+
5
-(2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl-2-((tert-butoxy-car
◦
1
bonyl)amino)-3-phenylpropanoate (4m). White solid. m.p.: 110–112 C. H-NMR (400 MHz, DMSO-d ):
6
δ
7.54 (d, 1H, J = 7.2 Hz), 7.48 (t, 1H, J = 7.2 Hz), 7.40–7.36 (m, 1H), 7.28–7.20 (m, 7 H), 6.32 (s, 1H), 4.76
(
1
[
s, 1H), 4.35–4.14 (m, 1H), 3.45–3.36 (m, 2H), 3.05–3.00 (m, 2H), 2.79–2.66 (m, 4H), 2.36–2.34 (m, 1H),
+
+
.31 (s, 9H), 0.87–0.76 (m, 4H). ESI-MS (m/z) = 579.17 [M+H] , HRMS(ESI) calcd. for C H FN O S :
32 36 2 5
+
M + H] m/z: 579.2323, found: 579.2315.