C26H36Cl2N5O3S [M+H]+: 568.1910; found 568.1924. Retention
time 2.59 min, > 99% pure.
5.1.58 N-(1-(3-(1-((4-chloro-3-fluorophenyl)amino)-5-oxo-
5,7,8,9-tetrahydro-6H-pyrido[4,3-c]azepin-6-
yl)propyl)piperidin-4-yl)-N-methylmethanesulfonamide (13p)
Following the similar procedures as for compound 13a gave
compound 13p, white solid, 55%. 1H NMR (400 MHz, CDCl3) δ
8.20 (d, J = 5.0 Hz, 1H), 7.58 (dd, J = 6.5, 2.7 Hz, 1H), 7.26 –
7.22 (m, 1H), 7.08 – 7.03 (m, 2H), 6.43 (s, 1H), 3.73 (tt, J = 11.9,
4.2 Hz, 1H), 3.61 – 3.54 (m, 2H), 3.23 (t, J = 6.4 Hz, 2H), 3.03 –
2.96 (m, 2H), 2.83 (s, 3H), 2.79 (s, 3H), 2.69 (t, J = 7.0 Hz, 2H),
2.43 – 2.37 (m, 2H), 2.08 – 1.99 (m, 4H), 1.86 – 1.81 (m, 4H),
1.72 – 1.65 (m, 2H). 13C NMR (126 MHz, CDCl3) δ 168.50,
153.13 (d, J = 243.7 Hz), 151.59, 146.00, 144.98, 137.29 (d, J =
2.8 Hz), 121.11, 120.31 (d, J = 18.5 Hz), 118.87 (d, J = 6.5 Hz),
116.39, 115.97 (d, J = 21.9 Hz), 114.58, 55.06, 54.46, 52.51,
45.71, 45.32, 38.02, 29.16, 28.25, 28.08, 26.06, 22.37. HRMS
(ESI): calcd for C25H34ClFN5O3S [M+H]+: 538.2049; found
538.2051. Retention time 2.29 min, > 98% pure.
5.1.62
1-((3,4-Dichlorophenyl)amino)-6-(3-(piperidin-1-
yl)propyl)-6,7,8,9-tetrahydro-5H-pyrido[4,3-c]azepin-5-one
(14c)
Following the similar procedures as for compound 13a gave
1
compound 14c, white solid, 53%. H NMR (400 MHz, CDCl3) δ
8.23 (d, J = 5.0 Hz, 1H), 7.67 (d, J = 2.5 Hz, 1H), 7.34 – 7.30 (m,
1H), 7.28 – 7.24 (m, 1H), 7.07 (d, J = 5.0 Hz, 1H), 6.55 (s, 1H),
3.61 – 3.54 (m, 2H), 3.23 (t, J = 6.4 Hz, 2H), 2.69 (t, J = 7.0 Hz,
2H), 2.48 – 2.35 (m, 6H), 2.10 – 1.99 (m, 2H), 1.91 – 1.81 (m,
2H), 1.64 – 1.56 (m, 4H), 1.48 – 1.40 (m, 2H). 13C NMR (126
MHz, CDCl3) δ 168.43, 151.15, 146.00, 145.14, 140.33, 131.99,
129.79, 124.18, 120.11, 118.09, 116.99, 115.01, 55.97, 54.13,
45.67, 45.37, 28.27, 25.75, 25.29, 23.77, 22.45. HRMS (ESI):
calcd for C23H29Cl2N4O [M+H]+: 447.1713; found 447.1725.
Retention time 2.50 min, > 95% pure.
5.1.59 N-(1-(3-(1-((3,5-dichlorophenyl)amino)-5-oxo-5,7,8,9-
tetrahydro-6H-pyrido[4,3-c]azepin-6-yl)propyl)piperidin-4-
yl)-N-methylmethanesulfonamide (13q)
5.1.63 1-((3,4-dichlorophenyl)amino)-6-(3-(4-phenylpiperidin-
1-yl)propyl)-6,7,8,9-tetrahydro-5H-pyrido[4,3-c]azepin-5-one
(14d)
Following the similar procedures as for compound 13a gave
compound 13q, white solid, 51%. 1H NMR (400 MHz, CDCl3) δ
8.27 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 1.8 Hz, 2H), 7.11 (d, J = 5.0
Hz, 1H), 6.95 (t, J = 1.8 Hz, 1H), 6.55 (s, 1H), 3.74 (tt, J = 11.8,
4.2 Hz, 1H), 3.61 – 3.54 (m, 2H), 3.23 (t, J = 6.4 Hz, 2H), 3.03 –
2.96 (m, 2H), 2.83 (s, 3H), 2.79 (s, 3H), 2.69 (t, J = 7.0 Hz, 2H),
2.43 – 2.36 (m, 2H), 2.08 – 1.99 (m, 4H), 1.87 – 1.78 (m, 4H),
1.72 – 1.64 (m, 2H). 13C NMR (126 MHz, CDCl3) δ 168.32,
150.84, 146.16, 145.23, 142.78, 134.58, 121.07, 117.41, 116.39,
115.50, 55.05, 54.46, 52.51, 45.67, 45.36, 38.03, 29.16, 28.26,
28.08, 26.06, 22.47. HRMS (ESI): calcd for C25H34Cl2N5O3S
[M+H]+: 554.1754; found 554.1763. Retention time 2.74 min, >
95% pure.
Following the similar procedures as for compound 13a gave
1
compound 14d, white solid, 65%. H NMR (400 MHz, CDCl3) δ
8.22 (d, J = 5.0 Hz, 1H), 7.67 (d, J = 2.4 Hz, 1H), 7.34 – 7.27 (m,
4H), 7.24 – 7.17 (m, 3H), 7.08 (d, J = 5.0 Hz, 1H), 6.63 (s, 1H),
3.65 – 3.56 (m, 2H), 3.24 (t, J = 6.3 Hz, 2H), 3.10 – 3.01 (m,
2H), 2.69 (t, J = 7.0 Hz, 2H), 2.55 – 2.39 (m, 3H), 2.11 – 1.99
(m, 4H), 1.94 – 1.74 (m, 6H). 13C NMR (126 MHz, CDCl3) δ
168.64, 151.37, 146.19, 145.93, 145.32, 140.54, 132.15, 129.97,
128.12, 126.53, 125.86, 124.34, 120.33, 118.33, 117.17, 115.17,
55.86, 54.19, 45.88, 45.63, 42.33, 33.15, 28.48, 26.23, 22.60.
HRMS (ESI): calcd for C29H33Cl2N4O [M+H]+: 523.2026; found
523.2033. Retention time 2.92 min, > 99% pure.
5.1.60 N-(1-(3-(1-((3,4-dichlorophenyl)amino)-5-oxo-5,7,8,9-
tetrahydro-6H-pyrido[4,3-c]azepin-6-yl)propyl)piperidin-4-
yl)methanesulfonamide (14a)
5.1.64 1-((3,4-Dichlorophenyl)amino)-6-(3-(spiro[indene-1,4'-
piperidin]-1'-yl)propyl)-6,7,8,9-tetrahydro-5H-pyrido[4,3-
c]azepin-5-one (14e)
Following the similar procedures as for compound 13a gave
compound 14a, white solid, 55%. 1H NMR (400 MHz, CDCl3) δ
8.24 (d, J = 5.0 Hz, 1H), 7.68 (d, J = 2.5 Hz, 1H), 7.34 – 7.26 (m,
2H), 7.07 (d, J = 5.0 Hz, 1H), 6.57 (s, 1H), 3.61 – 3.55 (m, 2H),
3.41 – 3.29 (m, 1H), 3.23 (t, J = 6.4 Hz, 2H), 2.98 (s, 3H), 2.95 –
2.88 (m, 2H), 2.71 (t, J = 7.0 Hz, 2H), 2.49 – 2.42 (m, 2H), 2.22
– 2.13 (m, 2H), 2.10 – 1.95 (m, 4H), 1.91 – 1.81 (m,2H), 1.70 –
1.58 (m, 2H). 13C NMR (126 MHz, CDCl3) δ 168.75, 151.40,
146.23, 145.20, 140.50, 132.18, 130.00, 124.42, 120.31, 118.30,
117.20, 115.14, 55.21, 51.73, 50.39, 45.97, 45.44, 41.83, 32.79,
28.46, 25.93, 22.64. HRMS (ESI): calcd for C24H32Cl2N5O3S
[M+H]+: 540.1597; found 540.1603. Retention time 2.47min, >
99% pure.
Following the similar procedures as for compound 13a gave
compound 14e, white solid, 49%. H NMR (400 MHz, CDCl3) δ
1
8.23 (d, J = 5.0 Hz, 1H), 7.68 (d, J = 2.5 Hz, 1H), 7.38 – 7.27 (m,
4H), 7.26 – 7.17 (m, 2H), 7.09 (d, J = 5.0 Hz, 1H), 6.84 (d, J =
5.7 Hz, 1H), 6.75 (d, J = 5.7 Hz, 1H), 6.60 (s, 1H), 3.68 – 3.59
(m, 2H), 3.26 (t, J = 6.3 Hz, 2H), 3.07 – 2.97 (m, 2H), 2.70 (t, J =
7.0 Hz, 2H), 2.57 – 2.50 (m, 2H), 2.40 – 2.28 (m, 2H), 2.24 –
2.17 (m, 2H), 2.11 – 2.02 (m, 3H), 1.97 – 1.88 (m, 2H), 1.40 –
1.33 (m, 2H). 13C NMR (126 MHz, CDCl3) δ 168.66, 151.88,
151.37, 146.22, 145.32, 142.59, 141.11, 140.53, 132.17, 129.99,
129.29, 126.55, 124.89, 124.37, 121.39, 121.03, 120.33, 118.32,
117.16, 115.19, 56.03, 52.15, 51.73, 45.90, 45.65, 33.57, 28.50,
26.27, 22.61. HRMS (ESI): calcd for C31H33Cl2N4O [M+H]+:
547.2026; found 547.2032. Retention time 3.02 min, > 99% pure.
5.1.61 N-(1-(3-(1-((3,4-dichlorophenyl)amino)-5-oxo-5,7,8,9-
tetrahydro-6H-pyrido[4,3-c]azepin-6-yl)propyl)piperidin-4-
yl)-N-methylethanesulfonamide (14b)
5.1.65
6-(3-(3H-spiro[benzo[c]thiophene-1,4'-piperidin]-1'-
yl)propyl)-1-((3,4-dichlorophenyl)amino)-6,7,8,9-tetrahydro-
5H-pyrido[4,3-c]azepin-5-one (14f)
Following the similar procedures as for compound 13a gave
Following the similar procedures as for compound 13a gave
compound 14b, white solid, 60%. 1H NMR (400 MHz, CDCl3) δ
8.23 (d, J = 5.0 Hz, 1H), 7.67 (d, J = 2.5 Hz, 1H), 7.34 – 7.27 (m,
2H), 7.07 (d, J = 5.0 Hz, 1H), 6.55 (s, 1H), 3.72 – 3.63 (m, 1H),
3.61 – 3.53 (m, 2H), 3.22 (t, J = 6.3 Hz, 2H), 3.03 – 2.92 (m,
4H), 2.79 (s, 3H), 2.69 (t, J = 7.0 Hz, 2H), 2.43 – 2.36 (m, 2H),
2.09 – 1.99 (m, 4H), 1.90 – 1.77 (m, 4H), 1.74 – 1.64 (m, 2H),
1.33 (t, J = 7.4 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 168.63,
151.37, 146.22, 145.26, 140.50, 132.16, 129.99, 124.40, 120.33,
118.32, 117.11, 115.16, 55.23, 54.50, 52.74, 45.97, 45.88, 45.50,
29.59, 28.49, 28.47, 26.20, 22.59, 7.93. HRMS (ESI): calcd for
1
compound 14f, white solid, 58%. H NMR (400 MHz, CDCl3) δ
8.24 (d, J = 5.0 Hz, 1H), 7.67 (d, J = 2.5 Hz, 1H), 7.35 – 7.30 (m,
1H), 7.28 – 7.20 (m, 6H), 7.09 (d, J = 5.0 Hz, 1H), 6.51 (s, 1H),
4.17 (s, 2H), 3.65 – 3.59 (m, 2H), 3.26 (t, J = 6.4 Hz, 2H), 3.04 –
2.98 (m, 2H), 2.71 (t, J = 7.0 Hz, 2H), 2.54 – 2.46 (m, 2H), 2.33
– 2.19 (m, 4H), 2.11 – 2.03 (m, 2H), 1.96 – 1.89 (m, 4H). 13C
NMR (126 MHz, CDCl3) δ 168.59, 151.31, 147.70, 146.26,
145.35, 140.48, 139.88, 132.22, 130.01, 127.07, 126.71, 124.84,
124.45, 122.80, 120.31, 118.27, 117.11, 115.29, 63.22, 55.69,
51.85, 45.86, 45.61, 40.59, 34.92, 28.49, 26.09, 22.66. HRMS