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solvent was further purified by silica gel column chromatogra- cyclopropyl –CH2), 1.51–1.57 (7H, brs, dipropylamine –CH2,
phy using methanol–chloroform) as the eluent. tetrahydropyran –CH2), 1.74 (3H, brs, tetrahydropyran –CH2),
1-Cyclopropyl-7-(4-dimethylaminomethyl-[1,2,3]triazol-1- 2.38–2.40 (4H, m, dipropylamine –NCH2), 3.58–3.61 (1H,
yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid m, tetrahydropyran –OCH2), 3.82–3.99 (4H, m, cyclopro-
(Tetrahydro-pyran-2-yloxy)amide (5a): This compound was pyl –CH, –CH2–N, tetrahydropyran –O–CH2), 4.99 (1H, s,
prepared by reaction of compound 4 with dimethyl amine tetrahydropyran –O–CH–O), 8.30 (1H, d, J=10.8Hz, ArH),
in the presence of triethylamine and potassium iodide. It 8.64–8.66 (2H, m, ArH), 8.74 (1H, s, triazole H), 12.04 (1H, s,
was obtained as a pale yellow solid (176mg, 87%), mp: –CONH); 13C-NMR (75MHz, DMSO-d6) δ: 8.44, 11.83, 18.35,
198.5–204.1°C; IR (ATR, cm−1) ν: 2937 (ArH), 1666 (amide 20.31, 25.06, 27.96, 35.30, 48.76, 55.85, 62.15, 102.06, 111.46,
1
–C=O), 1610 (–C=C), 1480 (–C–O), 1020 (–C–F); H-NMR 112.51, 114.62 (d, J=21.75Hz, C5-F coupling), 123.72 (d,
(DMSO-d6 300MHz) δ (ppm): 1.19–1.22 (2H, m, cyclopropyl J=11.25Hz, C10-F coupling), 127.43, 129.23 (d, J=12.75Hz,
–CH2), 1.31–1.33 (2H, m, cyclopropyl –CH2), 1.56 (3H, brs, C7-F coupling), 137.69, 147.34, 147.99, 148.52 and 151.83 (d,
tetrahydropyran –CH2), 1.73 (3H, brs, tetrahydropyran –CH2), J=248.25Hz, C6-F coupling), 161.97, 174.25; LC-MS (ESI,
2.25 (6H, s, –N(CH3)2), 3.58–3.61 (1H, m, tetrahydropyran m/z): 527.3 (M+H). Anal. Calcd for C27H35FN6O4: C, 61.58; H,
–OCH2), 3.69 (2H, s, –CH2–N), 3.87 (1H, brs, cyclopropyl 6.70; N, 15.96. Found: C, 61.61; H, 6.74; N, 15.94.
–CH), 3.99 (1H, brs, tetrahydropyran –O–CH2), 4.99 (1H, s,
tetrahydropyran –O–CH–O), 8.28 (1H, d, J=10.8Hz, ArH), [1,2,3]-triazol-1-yl)-1,4-dihydroquinoline-3-carboxylic
1-Cyclopropyl-6-fluoro-4-oxo-7-(4-piperidin-1-ylmethyl-
Acid
8.64–8.68 (2H, m, ArH), 8.73 (1H, s, triazole H), 12.02 (1H, (Tetrahydro-pyran-2-yloxy)amide (5d): This compound was
s, –CONH); 13C-NMR (75MHz, DMSO-d6) δ: 8.40, 18.36, prepared by reaction of compound 4 with piperidine in the
25.07, 27.97, 35.30, 45.08, 54.08, 60.42, 102.09, 111.51, 112.59, presence of triethylamine and potassium iodide. It was ob-
114.69 (d, J=21.75Hz, C5-F coupling), 124.08 (d, J=12.0Hz, tained as a off-white solid (160mg, 73%), mp 195.2–196.5°C;
C10-F coupling), 127.51 (d, J=6.75Hz, C7-F coupling), 129.20, IR (ATR, cm−1) ν: 2959 (ArH), 1668 (acid –C=O), 1614 (–C=
137.69, 146.21, 148.01, 148.54 & 151.80 (d, J=244.5Hz, C6-F C), 1477 (–C–O), 1025 (–C–F); 1H-NMR (DMSO-d6 300MHz)
coupling), 161.97, 174.22; LC-MS (ESI, m/z): 471.5 (M+H). δ (ppm): 1.19–1.23 (2H, m, cyclopropyl –CH2), 1.31–1.33 (2H,
Anal. Calcd for C23H27FN6O4: C, 58.71; H, 5.78; N, 17.86. m, cyclopropyl –CH2), 1.35–1.55 (9H, m, piperidine –CH2,
Found: C, 58.68; H, 5.80; N, 17.84.
1-Cyclopropyl-7-(4-diethylaminomethyl-[1,2,3]triazol-1- –CH2), 2.50 (4H, brs, piperidine –NCH2), 3.58–3.68 (3H, m,
yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid tetrahydropyran –OCH2, –CH2–N), 3.87 (1H, brs, cyclopro-
tetrahydropyran –CH2), 1.73 (3H, brs, tetrahydropyran
(Tetrahydro-pyran-2-yloxy)amide (5b): This compound was pyl –CH), 3.99 (1H, brs, tetrahydropyran –O–CH2), 4.99
prepared by reaction of compound 4 with diethyl amine (1H, s, tetrahydropyran –O–CH–O), 8.29 (1H, d, J=10.8Hz,
in the presence of triethylamine and potassium iodide. It ArH), 8.64–8.66 (2H, m, ArH), 8.73 (1H, s, triazole H), 12.04
was obtained as a pale yellow solid (170mg, 79%), mp (1H, s, –CONH); 13C-NMR (75MHz, DMSO-d6) δ: 8.44,
201.8–203.4°C; IR (ATR, cm−1) ν: 3010 (ArH), 1671 (amide 15.54, 18.36, 21.28, 25.08, 27.96, 35.31, 46.68, 54.12, 62.16,
1
–C=O), 1614 (–C=C), 1481 (–C–O), 1034 (–C–F); H-NMR 102.08, 111.46, 112.50, 114.69 (d, J=21.75Hz, C5-F coupling),
(DMSO-d6 300MHz) δ (ppm): 1.07 (6H, t, J=6.9Hz, di- 123.72 (d, J=11.25Hz, C10-F coupling), 127.45, 129.24 (d,
ethylamine –CH3), 1.19–1.23 (2H, m, cyclopropyl –CH2), J=6.75Hz, C7-F coupling), 137.70, 147.35, 148.52 and 151.83
1.31–1.33 (2H, m, cyclopropyl –CH2), 1.56 (3H, brs, tetrahy- (d, J=248.25Hz, C6-F coupling), 162.22, 174.24; LC-MS (ESI,
dropyran –CH2), 1.74 (3H, brs, tetrahydropyran –CH2), 2.50 m/z): 511.7 (M+H). Anal. Calcd for C26H31FN6O4: C, 61.16; H,
(4H, q, J=6.9Hz, diethylamine –NCH2), 3.58–3.61 (1H, m, 6.12; N, 16.46; Found: C, 61.20; H, 6.13; N, 16.44.
tetrahydropyran –OCH2), 3.87–3.99 (4H, m, cyclopropyl –CH,
–CH2–N, tetrahydropyran –O–CH2), 4.99 (1H, s, tetrahydro- triazol-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic
1-Cyclopropyl-6-fluoro-7-(4-morpholin-4-ylmethyl-[1,2,3]-
Acid
pyran –O–CH–O), 8.28 (1H, d, J=10.8Hz, ArH), 8.64–8.66 (Tetrahydro-pyran-2-yloxy)amide (5e): This compound was
(2H, m, ArH), 8.73 (1H, s, triazole H), 12.02 (1H, s, –CONH); prepared by reaction of compound 4 with morpholine in the
13C-NMR (75MHz, DMSO-d6) δ: 8.41, 14.54, 18.37, 25.07, presence of triethylamine and potassium iodide. It was ob-
27.96, 35.32, 46.23, 55.12, 62.21, 102.07, 111.46, 112.51, 114.69 tained as pale yellow solid (196mg, 89%), mp 192.6–193.5°C;
(d, J=21.75Hz, C5-F coupling), 123.72 (d, J=11.20Hz, C10-F IR (ATR, cm−1) ν: 2939 (ArH), 1670 (amide –C=O), 1612
coupling), 127.43, 129.21 (d, J=12.70Hz, C7-F coupling), (–C=C), 1478 (–C–O), 1024 (–C–F); 1.19–1.23 (2H, m, cy-
137.69, 147.34, 148.51 & 151.82 (d, J=248.25Hz, C6-F cou- clopropyl –CH2), 1.31–1.33 (2H, m, cyclopropyl –CH2), 1.56
pling), 162.32, 174.24; LC-MS (ESI, m/z): 499.6 (M+H). Anal. (3H, brs, tetrahydropyran –CH2), 1.73 (3H, brs, tetrahydro-
Calcd for C25H31FN6O4: C, 60.23; H, 6.27; N, 16.86. Found: C, pyran –CH2), 3.33 (4H, brs, morpholine –NCH2), 3.59 (5H,
60.25; H, 6.31; N, 16.83.
1-Cyclopropyl-7-(4-dipropylaminomethyl-[1,2,3]triazol-1- s, –CH2–N), 3.86 (1H, brs, cyclopropyl –CH), 3.99 (1H,
yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid brs, tetrahydropyran –O–CH2), 4.99 (1H, s, tetrahydropyran
brs, tetrahydropyran –OCH2, morpholine –OCH2), 3.71 (2H,
(Tetrahydro-pyran-2-yloxy)amide (5c): This compound was –O–CH–O), 8.28 (1H, d, J=10.8Hz, ArH), 8.64–8.69 (2H,
prepared by reaction of compound 4 with dipropyl amine in m, ArH), 8.73 (1H, s, triazole H), 12.03 (1H, s, –CONH);
the presence of triethylamine and potassium iodide. It was ob- 13C-NMR (75MHz, DMSO-d6) δ: 8.40, 18.37, 25.07, 27.97,
tained as an off-white solid (175mg, 77%), mp 183.2–187.8°C; 35.31, 48.76, 55.12, 62.14, 62.43, 73.11, 102.09, 111.47, 112.50,
IR (ATR, cm−1) ν: 2957 (ArH), 1668 (amide –C=O), 1609 114.64 (d, J=21.75Hz, C5-F coupling), 123.70, (d, J=13.50Hz,
(–C=C), 1476 (–C–O), 1018 (–C–F); 1H-NMR (DMSO-d6 C10-F coupling), 127.42, 129.22 (d, J=12.75Hz, C7-F cou-
300MHz) δ (ppm): 0.86 (6H, t, J=7.2Hz, dipropylamine pling), 137.70, 147.32, 148.53 and 151.84 (d, J=248.25Hz,
–CH3), 1.20 (2H, brs, cyclopropyl –CH2), 1.30–1.33 (2H, m, C6-F coupling), 162.42, 174.26; LC-MS (ESI, m/z): 513.2 (M+