Journal of Medicinal Chemistry
ARTICLE
Hz, 2H), 5.21 (s, 2H). MS calcd for C26H19Cl2NO4S, 511.0412; found,
511.90, (Supporting Information).
1H NMR (DMSO-d6, 600 MHz): 8.23 (s, 2H), 8.06
(s, 1H), 8.01 (d, J = 8.4 Hz, 2H), 7.98 (d, J = 7.8 Hz, 1H), 7.86
(d, J = 7.8 Hz, 1H), 7.78ꢀ7.75 (m, 2H), 7.59 (t, J1 = 7.2 Hz, J2 = 7.8 Hz,
1H), 7.47 (t, J1 = 7.8 Hz, J2 = 7.2 Hz, 2H), 7.27 (t, J1 = 7.8 Hz, J2 = 7.2 Hz,
1H), 7.16ꢀ7.13 (m, 4H). HRMS calcd for C25H17Cl2NO4S, 498.0328 (M +
H); found, 498.0317. HPLC purity 99.3%, tR = 14.84 min.
20,40-Dichloro-N-((4-(phenoxymethyl)phenyl)sulfonyl)-
[1,10-biphenyl]-3-carboxamide (17). Compound 17 was obtained
according to the procedure given for the general solution coupling from
20,40-dichloro-[1,10-biphenyl]-3-carboxylic acid and 6a (Supporting In-
formation). 1H NMR (DMSO-d6, 600 MHz): 8.01 (d, J = 6.6 Hz, 2H),
7.92ꢀ7.90 (m, 3H), 7.76 (s, 1H), 7.68 (m, 3H), 7.58ꢀ7.54 (m, 2H),
7.50 (d, J = 8.4 Hz, 1H), 7.29 (t, J1 = 7.2 Hz, J2 = 7.8 Hz, 2H), 7.01 (d, J =
7.8 Hz, 2H), 6.94 (t, J1 = 7.2 Hz, J2 = 7.8 Hz, 1H), 5.21 (s, 2H). HRMS
calcd for C26H19Cl2NO4S, 534.0304 (M + Na); found, 534.0303. HPLC
purity 99.0%, tR = 14.34 min.
20,30-Dichloro-N-((4-phenoxyphenyl)sulfonyl)-[1,10-bi-
phenyl]-3-carboxamide (24). Compound 24 was obtained accord-
ing to the procedure given for the general solution coupling from 20,30-
dichloro-[1,10-biphenyl]-3-carboxylic acid and 6b (Supporting In-
1
formation). H NMR (DMSO-d6, 600 MHz): 7.98 (d, J = 7.8 Hz,
2H), 7.94ꢀ7.92 (m, 3H), 7.70 (d, J = 7.8 Hz, 2H), 7.56 (m, 1H), 7.47 (t,
J1 = 7.2 Hz, J2 = 7.8 Hz, 3H), 7.42 (d, J = 7.8 Hz, 1H), 7.26 (m, 1H), 7.15
(d, J = 7.8 Hz, 2H), 7.12 (d, J = 7.8 Hz, 2H). HRMS calcd for
C25H17Cl2NO4S, 498.0328 (M + H); found, 498.0336. HPLC purity
98.3%, tR = 13.83 min.
30,40-Dichloro-N-((4-(phenoxymethyl)phenyl)sulfonyl)-
[1,10-biphenyl]-3-carboxamide (18). Compound 18 was obtained
according to the procedure given for the general solution coupling from
30,40-dichloro-[1,10-biphenyl]-3-carboxylic acid and 6a (Supporting In-
formation). 1H NMR (DMSO-d6, 600 MHz): 8.17 (s, 1H), 7.92ꢀ7.88
(m, 4H), 7.76 (m, 1H), 7.71 (d, J = 8.4 Hz, 1H), 7.67 (d, J = 8.4 Hz, 1H),
7.51 (m, 2H), 7.46 (m, 1H), 7.28 (t, J1 = 7.8 Hz, J2 = 7.8 Hz, 2H), 7.0 (d,
J = 7.8 Hz, 2H), 6.93 (t, J1 = 6.6 Hz, J2 = 7.8 Hz, 1H), 5.14 (s, 2H).
HRMS calcd for C26H19Cl2NO4S, 534.0304 (M + Na); found,
534.0405. HPLC purity 99.4%, tR = 14.56 min.
30,40-Dimethoxy-N-((4-phenoxyphenyl)sulfonyl)-[1,10-bi-
phenyl]-3-carboxamide (25). Compound 25 was obtained accord-
ing to the procedure given for the general solution coupling from 30,40-
dimethoxy-[1,10-biphenyl]-3-carboxylic acid and 6b (Supporting In-
1
formation). H NMR (DMSO-d6, 600 MHz): 8.12 (s, 2H), 8.01 (d,
J = 8.4 Hz, 2H), 7.90 (d, J = 7.2 Hz, 1H), 7.78 (d, J = 7.8 Hz, 1H), 7.54 (t,
J1 = 7.2 Hz, J2 = 7.8 Hz, 1H), 7.47 (t, J1 = 7.8 Hz, J2 = 7.2 Hz, 2H), 7.28
(m 3H), 7.15 (m, 3H), 7.06 (d, J = 7.8 Hz, 1H), 3.85 (s, 3H), 3.80 (s,
3H). HRMS calcd for C27H23NO6S, 490.1319 (M + H); found,
490.1332. HPLC purity 99.7%, tR = 10.27 min.
N-((4-Phenoxyphenyl)sulfonyl)-[1,10-biphenyl]-3-carbox-
amide (19). Compound 19 was obtained according to the procedure
given for the general solution coupling from [1,10-biphenyl]-3-car-
1
boxylic acid and 6b (Supporting Information). H NMR (DMSO-d6,
600 MHz): 8.20 (s, 1H), 8.01 (d, J = 8.4 Hz, 2H), 7.92 (d, J = 6.6 Hz,
1H), 7.83 (d, J = 7.8 Hz, 1H), 7.75 (d, J = 7.8 Hz, 2H), 7.58 (t, J1 =7.2 Hz,
J2 = 7.8 Hz, 1H), 7.51ꢀ7.46 (m, 4H), 7.42 (m, 1H), 7.27 (m, 1H),
7.17ꢀ7.13 (m, 4H). HRMS calcd for C25H19NO4S, 430.1107 (M + H);
found, 430.1125. HPLC purity 99.0%, tR = 11.84 min.
30,40-Dichloro-N-(naphthalen-2-ylsulfonyl)-[1,10-biphenyl]-
3-carboxamide (26). Compound 26 was obtained according to the
procedure given for the general solution coupling from 30,40-
dichloro-[1,10-biphenyl]-3-carboxylic acid and naphthalene-2-sulfonam-
ide. 1H NMR (DMSO-d6, 600 MHz): 8.71 (s, 1H), 8.25 (m, 2H), 8.16 (d,
J = 8.4 Hz, 1H), 8.06 (m, 2H), 7.98 (m, 2H), 7.83 (d, J = 7.8 Hz, 1H), 7.75
(m, 4H), 7.70 (t, J1 = 7.8 Hz, J2 = 7.2 Hz, 1H), 7.57 (t, J1 = 7.8 Hz, J2 = 7.2
Hz, 1H). MS calcd for C23H15Cl2NO3S, 455.0150; found, 455.90
(Supporting Information).
30,50-Dichloro-N-((4-phenoxyphenyl)sulfonyl)-[1,10-bi-
phenyl]-3-carboxamide (20). Compound 20 was obtained accord-
ing to the procedure given for the general solution coupling from 30,50-
dichloro-[1,10-biphenyl]-3-carboxylic acid and 6b (Supporting In-
1
formation). H NMR (DMSO-d6, 600 MHz): 8.24 (s, 2H), 8.02ꢀ8.0
N-((4-Butoxyphenyl)sulfonyl)-30,40-dichloro-[1,10-biphenyl]-
3-carboxamide (27). Compound 27 was obtained according to the
procedure given for the general solution coupling from 30,40-dichloro-[1,10-
(m, 3H), 7.88ꢀ7.84 (m, 3H), 7.66 (s, 1H), 7.60 (t, J1 = 7.2 Hz, J2 = 7.8
Hz, 1H), 7.27 (m, 1H), 7.16ꢀ7.13 (m, 4H). HRMS calcd for
C25H17Cl2NO4S, 498.0328 (M + H); found, 498.0327. HPLC purity
97.1%, tR = 15.24 min.
1
biphenyl]-3-carboxylic acid and 4-butoxybenzenesulfonamide. H NMR
(DMSO-d6, 600 MHz): 8.19 (s, 1H), 7.97 (m, 3H), 7.73 (m, 3H), 7.72 (d,
J = 7.8 Hz, 2H), 7.61 (t, J1 = 7.8 Hz, J2 = 7.8 Hz, 1H), 7.06 (d, J = 7.8 Hz,
2H), 4.03 (t, J1 = 6.0 Hz, J2 = 6.0 Hz, 2H), 1.69 (m, 2H), 1.42 (m, 2H), 0.92
(t, J1 = 7.2 Hz, J2 = 7.2 Hz, 3H). MS calcd for C23H21Cl2NO4S, 477.0568;
found, 477.90 (Supporting Information).
N-((4-(Benzyloxy)phenyl)sulfonyl)-30,40-dichloro-[1,10-bi-
phenyl]-3-carboxamide (28). Compound 28 was obtained ac-
cording to the procedure given for the general solution coupling from
30,40-dichloro-[1,10-biphenyl]-3-carboxylic acid and 4 (benzyloxy)benzene-
sulfonamide. 1H NMR (DMSO-d6, 600 MHz): 12.51 (s, 1H), 8.22 (s, 1H),
8.06 (s, 1H), 7.95 (m, 3H), 7.84 (d, J = 7.8 Hz, 1H), 7.76 (m, 2H), 7.58 (m,
1H), 7.46 (d, J = 7.2 Hz, 2H), 7.40 (t, J1 = 7.2 Hz, J2 = 7.2 Hz, 2H), 7.34 (m,
1H), 7.23 (d, J = 7.8 Hz, 2H), 5.21 (s, 2H). MS calcd for C26H19Cl2NO4S,
511.0412; found, 511.85 (Supporting Information).
30,40-Dichloro-N-((4-(cyclohexylmethoxy)phenyl)sulfonyl)-
[1,10-biphenyl]-3-carboxamide (29). Compound 29 was obtained
according to the procedure given for the general solution coupling from
30,40-dichloro-[1,10-biphenyl]-3-carboxylic acid and 4-(cyclohexylmethoxy)-
benzenesulfonamide. 1H NMR (DMSO-d6, 600 MHz): 12.53 (s, 1H), 8.21
(s, 1H), 8.06 (s, 1H), 7.97 (d, J = 7.2 Hz, 1H), 7.93 (d, J = 8.4 Hz, 2H), 7.84
(d, J = 7.2 Hz, 1H), 7.76 (m, 2H), 7.58 (t, J1 = 7.8 Hz, J2 = 7.2 Hz, 1H), 7.13
(d, J = 8.4 Hz, 2H), 3.88 (d, J = 6.0 Hz, 2H), 1.75 (m, 4H), 1.64 (d, J = 12.0
Hz, 1H), 1.20 (m, 4H), 1.03 (m, 2H). MS calcd for C26H25Cl2NO4S,
517.0881; found, 517.90 (Supporting Information).
30,50-Dichloro-N-((6-phenoxypyridin-3-yl)sulfonyl)-[1,10-
biphenyl]-3-carboxamide (21). Compound 21 was obtained ac-
cording to the procedure given for the general solution coupling from
30,50-dichloro-[1,10-biphenyl]-3-carboxylic acid and 6b (Supporting
1
Information). H NMR (DMSO-d6, 600 MHz): 8.60 (bs, 1H), 8.30
(bs, 1H), 8.20 (s, 1H), 7.92 (d, J = 7.2 Hz, 1H), 7.86 (bs, 1H), 7.56 (m,
2H), 7.62 (s, 1H), 7.27 (m, 1H), 7.51 (bs, 1H), 7.44 (m, 2H), 7.25 (t,
J1 = 7.2 Hz, J2 = 7.2 Hz, 1H), 7.18 (d, J = 7.2 Hz, 2H), 7.11 (bs, 1H).
HRMS calcd for C24H16Cl2N2O4S, 499.0281 (M + H); found,
499.0285. HPLC purity 95.4%, tR = 14.31 min.
20,40-Dichloro-N-((4-phenoxyphenyl)sulfonyl)-[1,10-bi-
phenyl]-3-carboxamide (22). Compound 22 was obtained accord-
ing to the procedure given for the general solution coupling from 20,
40-dichloro-[1,10-biphenyl]-3-carboxylic acid and 6b (Supporting
Information). 1H NMR (DMSO-d6, 600 MHz): 7.99 (d, J = 8.4 Hz, 2H),
7.93ꢀ7.91 (m, 3H), 7.77 (s, 1H), 7.71 (d, J = 7.2 Hz, 1H), 7.59 (t, J1 =
7.8 Hz, J2 = 7.2 Hz, 1H), 7.55 (d, J = 7.8 Hz, 1H), 7.51 (d, J = 8.4 Hz,
1H), 7.47(t, J1 = 7.8 Hz, J2 = 7.2 Hz, 2H), 7.27(t, J1 = 7.8 Hz, J2 = 7.2 Hz,
1H), 7.16ꢀ7.12 (m, 4H). HRMS calcd for C25H17Cl2NO4S, 498.0328
(M + H); found, 498.0351. HPLC purity 99.0%, tR = 14.56 min.
30,40-Dichloro-N-((4-phenoxyphenyl)sulfonyl)-[1,10-bi-
phenyl]-3-carboxamide (23). Compound 23 was obtained according
to the procedure given for the general solution coupling from 30,40-
dichloro-[1,10-biphenyl]-3-carboxylic acid and 6b (Supporting Information).
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dx.doi.org/10.1021/jm200826s |J. Med. Chem. 2011, 54, 6000–6013