The Journal of Organic Chemistry
Article
aminoquinoline.3b Amide 1m was synthesized by the condensation of
8-aminoquinoline with 4-(benzyl(tert-butoxycarbonylamino)-butanoic
acid using EDCI and HOBt.16a,b Other amides were synthesized
according to literature procedures.16c
6-(Benzyloxy)-N-(quinolin-8-yl)hexanamide (1i). 1H NMR
(400 MHz, CDCl3, ppm): δ = 9.80 (s, 1H), 8.94−8.65 (m, 2H),
8.14 (dd, J = 8.3, 1.5 Hz, 1H), 7.56−7.46 (m, 2H), 7.43 (dd, J = 8.3,
4.2 Hz, 1H), 7.35−7.31 (m, 4H), 7.30−7.22 (m, 1H), 4.49 (s, 2H),
3.49 (t, J = 6.5 Hz, 2H), 2.57 (t, J = 7.6 Hz, 2H), 1.85 (dt, J = 15.3, 7.6
Hz, 2H), 1.71 (dt, J = 14.5, 6.7 Hz, 2H), 1.60−1.45 (m, 2H); 13C{1H}
NMR (100 MHz, CDCl3, ppm): δ = 171.8, 148.2, 138.7, 138.4, 136.5,
134.7, 128.5, 128.1, 127.7, 127.6, 127.5, 121.7, 121.5, 116.5, 73.0, 70.3,
38.3, 29.7, 26.0, 25.6; HRMS (ESI) m/z Calcd for C22H25N2O2 (M +
H)+: 349.1910, found: 349.1910; IR (neat, cm−1) ν = 3354, 2925,
1683, 1528, 1099, 796, 747.
6-((tert-Butyldimethylsilyl)oxy)-N-(quinolin-8-yl)hexanamide
(1j). 1H NMR (300 MHz, CDCl3, ppm): δ = 9.81 (s, 1H), 8.88−8.70
(m, 2H), 8.14 (dd, J = 8.1, 1.5 Hz, 1H), 7.58−7.42 (m, 3H), 3.63 (t, J
= 6.3 Hz, 2H), 2.57 (t, J = 7.5 Hz, 2H), 1.90−1.75 (m, 2H), 1.66−1.56
(m, 2H), 1.53−1.42 (m, 2H), 0.88 (s, 9H), 0.04 (s, 6H); 13C{1H}
NMR (75 MHz, CDCl3, ppm): δ = 171.9, 148.2, 138.5, 136.5, 134.7,
128.1, 127.6, 121.7, 121.4, 116.5, 63.1, 38.4, 32.7, 26.1, 25.7, 25.6, 18.5,
−5.2; HRMS (ESI) m/z Calcd for C21H33N2O2Si (M + H)+:
373.2305, found: 373.2303; IR (neat, cm−1) ν = 3440, 2925, 1634,
1520, 1475, 1258, 1095, 833, 780.
N-(Quinolin-8-yl)butyramide (1a). 1H NMR (400 MHz, CDCl3,
ppm): δ = 9.80 (s, 1H), 9.00−8.59 (m, 2H), 8.16 (d, J = 1.6 Hz, 1H),
7.56−7.47 (m, 2H), 7.44 (dd, J = 8.3, 4.2 Hz, 1H), 2.54 (t, J = 7.5 Hz,
2H), 1.94−1.77 (m, 2H), 1.06 (t, J = 7.4 Hz, 3H); 13C{1H} NMR
(100 MHz, CDCl3, ppm): δ = 171.9, 148.2, 138.5, 136.5, 134.7, 128.1,
127.6, 121.7, 121.4, 116.5, 40.3, 19.3, 14.0. The spectral data of the
compound (1a) were in accordance with those reported in the
literature.3b
N-(Quinolin-8-yl)heptanamide (1b). 1H NMR (400 MHz,
CDCl3, ppm): δ = 9.80 (s, 1H), 8.95−8.64 (m, 2H), 8.14 (d, J =
8.3 Hz, 1H), 7.60−7.35 (m, 3H), 2.56 (t, J = 7.6 Hz, 2H), 1.88−1.71
(m, 2H), 1.38−1.32 (m, 6H), 0.89 (t, J = 6.8 Hz, 3H); 13C{1H} NMR
(100 MHz, CDCl3, ppm): δ = 172.1, 148.2, 138.5, 136.5, 134.7, 128.1,
127.6, 121.7, 121.4, 116.5, 77.5, 77.2, 76.8, 38.4, 31.7, 29.1, 25.8, 22.7,
14.2. The spectral data of the compound (1b) were in accordance with
those reported in the literature.3f
1
N-(Quinolin-8-yl)stearamide (1c). H NMR (400 MHz, CDCl3,
ppm): δ = 9.81 (s, 1H), 8.93−8.68 (m, 2H), 8.16 (dd, J = 8.3, 1.4 Hz,
1H), 7.69−7.32 (m, 3H), 2.56 (t, J = 7.6 Hz, 2H), 1.87−1.73 (m, 2H),
1.48−1.18 (m, 28H), 0.88 (t, J = 6.8 Hz, 3H); 13C{1H} NMR (100
MHz, CDCl3, ppm): δ = 172.1, 148.2, 138.5, 136.5, 134.8, 128.1,
127.6, 121.7, 121.4, 116.6, 38.5, 32.1, 29.8, 29.7, 29.6, 29.5, 29.5, 25.9,
22.8, 14.3; HRMS (ESI) m/z Calcd for C27H43N2O (M + H)+:
411.3369, found: 411.3370; IR (neat, cm−1) ν = 3289, 2920, 1675,
1530, 1474, 1326, 790.
tert-Butyl (6-Oxo-6-(quinolin-8-ylamino)hexyl)carbamate
1
(1k). H NMR (400 MHz, CDCl3, ppm): δ = 9.79 (s, 1H), 8.78−
8.66 (m, 2H), 8.14 (dd, J = 8.3, 1.5 Hz, 1H), 7.65−7.30 (m, 3H), 4.60
(br, 1H), 3.13 (d, J = 6.3 Hz, 2H), 2.55 (t, J = 7.5 Hz, 2H), 1.89−1.75
(m, 2H), 1.54 (dd, J = 14.4, 7.5 Hz, 2H), 1.48−1.35 (m, 11H);
13C{1H} NMR (100 MHz, CDCl3, ppm): δ = 171.7, 156.1, 148.2,
138.4, 136.5, 134.6, 128.1, 127.5, 121.7, 121.5, 116.5, 79.1, 40.5, 38.1,
30.0, 28.5, 26.6, 25.3; HRMS (ESI) m/z Calcd for C20H28N3O3 (M +
H)+: 358.2125, found: 358.2126; IR (neat, cm−1) ν = 3353, 2933,
1697, 1533, 1378, 1325, 1256, 1169, 787.
6-(1,3-Dioxoisoindolin-2-yl)-N-(quinolin-8-yl)hexanamide
(1l). 1H NMR (400 MHz, CDCl3, ppm): δ = 9.78 (s, 1H), 8.87−8.66
(m, 2H), 8.14 (d, J = 8.3 Hz, 1H), 7.81 (dt, J = 6.7, 3.4 Hz, 2H), 7.73−
7.64 (m, 2H), 7.55−7.39 (m, 3H), 3.70 (t, J = 7.2 Hz, 2H), 2.56 (t, J =
7.5 Hz, 2H), 1.93−1.68 (m, 4H), 1.56−1.43 (m, 2H); 13C{1H} NMR
(100 MHz, CDCl3, ppm): δ = 171.6, 168.5, 148.2, 138.4, 136.5, 134.6,
134.0, 132.3, 128.0, 127.5, 123.3, 121.7, 121.5, 116.5, 38.0, 38.0, 28.6,
26.7, 25.3. The spectral data of the compound (1l) were in accordance
with those reported in the literature.16d
3-(4-Bromophenyl)-N-(quinolin-8-yl)propanamide (1d). 1H
NMR (400 MHz, CDCl3, ppm): δ = 9.76 (s, 1H), 8.77 (d, J = 4.6
Hz, 2H), 8.14 (d, J = 8.3 Hz, 1H), 7.57−7.46 (m, 2H), 7.46−7.37 (m,
3H), 7.16 (d, J = 8.0 Hz, 2H), 3.09 (t, J = 7.6 Hz, 2H), 2.85 (t, J = 7.6
Hz, 2H); 13C{1H} NMR (100 MHz, CDCl3, ppm): δ = 170.4, 148.2,
139.9, 138.4, 136.5, 134.4, 131.7, 130.3, 128.0, 127.5, 121.7, 121.7,
120.2, 116.6, 39.5, 30.9. The spectral data of the compound (1d) were
in accordance with those reported in the literature.16c
4-Phenyl-N-(quinolin-8-yl)butanamide (1e). 1H NMR (400
MHz, CDCl3, ppm): δ = 9.79 (s, 1H), 8.87−8.71 (m, 2H), 8.14 (d, J =
8.3 Hz, 1H), 7.60−7.37 (m, 3H), 7.36−7.12 (m, 5H), 2.77 (t, J = 7.5
Hz, 2H), 2.57 (t, J = 7.4 Hz, 2H), 2.22−2.07 (m, 2H); 13C {1H} NMR
(100 MHz, CDCl3, ppm): δ = 171.6, 148.2, 141.6, 138.4, 136.5, 134.6,
128.7, 128.5, 128.0, 127.5, 126.1, 121.7, 121.5, 116.6, 37.4, 35.3, 27.2.
The spectral data of the compound (1e) were in accordance with
those reported in the literature.16c
tert-Butyl Benzyl(4-oxo-4-(quinolin-8-ylamino)butyl)-
1
carbamate (1m). H NMR (400 MHz, CDCl3, ppm): δ = 9.79 (s,
1H), 8.98−8.61 (m, 2H), 8.14 (d, J = 8.0 Hz, 1H), 7.56−7.47 (m,
2H), 7.44 (dd, J = 8.2, 4.2 Hz, 1H), 7.35−7.15 (m, 5H), 4.48 (s, 2H),
3.45−3.20 (m, 2H), 2.65−2.40 (m, 2H), 2.15−1.90 (m, 2H), 1.44 (s,
9H); 13C{1H} NMR (100 MHz, CDCl3, ppm): δ = 171.2, 171.1,
156.1, 148.2, 138.5, 136.4, 134.6, 128.59, 128.1, 127.8, 127.5, 127.3,
121.7, 121.5, 116.6, 79.9, 50.5, 50.1, 46.0, 35.3, 28.5, 24.0. The spectral
data of the compound (1m) were in accordance with those reported in
the literature.16b
4-Methyl-N-(quinolin-8-yl)pentanamide (1f). 1H NMR (400
MHz, CDCl3, ppm): δ = 9.81 (s, 1H), 8.90−8.73 (m, 2H), 8.15 (d, J =
8.2 Hz, 1H), 7.57−7.47 (m, 2H), 7.45 (dd, J = 8.2, 4.2 Hz, 1H), 2.78−
2.33 (m, 2H), 1.85−1.49 (m, 3H), 0.98 (d, J = 5.9 Hz, 6H); 13C{1H}
NMR (100 MHz, CDCl3, ppm): δ = 172.2, 148.2, 138.5, 136.5, 134.7,
128.1, 127.6, 121.7, 121.4, 116.6, 36.4, 34.6, 28.0, 22.5. The spectral
data of the compound (1f) were in accordance with those reported in
the literature.16b
Methyl 6-Oxo-6-(quinolin-8-ylamino)hexanoate (1n). 1H
NMR (400 MHz, CDCl3, ppm): δ = 9.80 (s, 1H), 8.90−8.70(m,
5.7 Hz, 2H), 8.15 (d, J = 8.3 Hz, 1H), 7.57−7.41 (m, 3H), 3.66 (s,
3H), 2.58 (t, J = 7.2 Hz, 2H), 2.40 (t, J = 7.2 Hz, 2H), 1.92−1.71 (m,
4H); 13C{1H} NMR (100 MHz, CDCl3, ppm): δ = 174.0, 171.3,
148.3, 138.4, 136.5, 134.6, 128.1, 127.6, 121.7, 121.5, 116.6, 51.7, 37.8,
34.0, 25.2, 24.7. The spectral data of the compound (1n) were in
accordance with those reported in the literature.16b
(R)-N-(Quinolin-8-yl)-4-((3R,5S,7R,8R,9S,10S,12S,13R,-
14S,17R)-3,7,12-trimethoxy-10,13-dimethylhexadecahydro-
1H-cyclopenta[a]phenanthren-17-yl)pentanamide (1o). 1H
NMR (400 MHz, CDCl3, ppm): δ = 9.81 (s, 1H), 8.95−8.59 (m,
2H), 8.15 (dd, J = 8.2, 1.3 Hz, 1H), 7.64−7.34 (m, 3H), 3.38 (s, 1H),
3.33 (s, 3H), 3.27 (s, 3H), 3.21 (s, 3H), 3.14 (d, J = 2.5 Hz, 1H),
3.04−2.93 (m, 1H), 2.61 (dd, J = 10.3, 4.8 Hz, 1H), 2.47 (dd, J = 10.6,
4.2 Hz, 1H), 2.28−1.86 (m, 6H), 1.86−1.40 (m, 11H), 1.38−1.11 (m,
5H), 1.09−0.78 (m, 9H), 0.67 (s, 3H); 13C{1H} NMR (100 MHz,
CDCl3, ppm): δ = 172.6, 148.2, 138.5, 136.5, 134.8, 128.1, 127.6,
121.7, 121.3, 116.5, 82.2, 80.9, 56.0, 55.8, 55.5, 46.5, 46.3, 42.8, 42.1,
39.8, 35.4, 35.3, 35.1, 35.0, 34.6, 31.7, 28.1, 27.9, 27.6, 26.9, 23.3, 23.0,
3-Cyclopentyl-N-(quinolin-8-yl)propanamide (1g). 1H NMR
(400 MHz, CDCl3, ppm): δ = 9.81 (s, 1H), 8.90−8.70 (m, 2H), 8.15
(d, J = 8.2 Hz, 1H), 7.58−7.47 (m, 2H), 7.44 (dd, J = 8.2, 4.2 Hz, 1H),
2.67−2.49 (m, 2H), 1.87 (m, 5H), 1.72−1.43 (m, 4H), 1.33−1.00 (m,
2H); 13C{1H} NMR (100 MHz, CDCl3, ppm): δ = 172.2, 148.2,
138.5, 136.5, 134.7, 128.1, 127.6, 121.7, 121.4, 116.6, 39.9, 37.7, 32.7,
32.0, 25.3. The spectral data of the compound (1g) were in accordance
with those reported in the literature.16d
3-Cyclohexyl-N-(quinolin-8-yl)propanamide (1h). 1H NMR
(400 MHz, CDCl3, ppm): δ = 9.80 (s, 1H), 8.90−8.68 (m, 2H), 8.15
(dd, J = 8.3, 1.4 Hz, 1H), 7.51 (dt, J = 8.2, 7.5 Hz, 2H), 7.45 (dd, J =
8.3, 4.2 Hz, 1H), 2.64−2.51 (m, 2H), 1.87−1.58 (m, 7H), 1.42−1.31
(m, 1H), 1.31−1.11 (m, 3H), 1.04−0.89 (m, 2H); 13C{1H} NMR
(100 MHz, CDCl3, ppm): δ = 172.3, 148.2, 138.5, 136.5, 134.8, 128.1,
127.6, 121.7, 121.4, 116.5, 37.5, 35.9, 33.3, 33.2, 26.7, 26.4. The
spectral data of the compound (1h) were in accordance with those
reported in the literature.16c
F
J. Org. Chem. XXXX, XXX, XXX−XXX