1154 Journal of Medicinal Chemistry, 2007, Vol. 50, No. 6
DaVey et al.
2H), 2.60 (m, 1H), 2.40 (m, 1H), 1.95 (s, 2H), 1.30 (m, 6H). Anal.
(C25H29N7O5‚0.5H2O) C, H, N.
H), 5.15 (br, 1 H), 4.3 (m, 1 H), 2.95 (m, 1 H), 2.65 (dd, 1 H),
2.55 (dd, 1 H), 1.3-1.8 (m, 6 H). Anal. (C24H24N6O‚0.2H2O) C,
H, N.
N-[(4-Chlorophenyl)methyl]-1-[2-(1H-imidazol-1-yl)pyrimi-
din-4-yl]-2-piperidineacetamide (12h). 1H NMR (CDCl3) δ 8.65
(br, 1 H), 8.05 (d, 1 H), 7.8 (s, 1 H), 7.4 (br, 1 H), 7.0 (m, 5 H),
6.5 (m, 1 H), 5.2 (br, 1 H), 4.2 (m, 2 H), 3.65 (m, 1H), 3.05 (m, 1
H), 2.75 (dd, 1 H), 2.6 (dd, 1 H), 1.3-1.8 (m, 6 H). Anal. (C21H23N6-
OCl‚0.8H2O) C, H, N.
N-[(1,3-Benzodioxol-5-yl)methyl]-1-[2-(1H-imidazol-1-yl)py-
rimidin-4-yl]-4-(6-fluoropyridin-2-yl)-2-piperazineacetamide (11t).
1H NMR (DMSO-d6) δ 8.5 (s, 1 H), 8.4 (m, 1 H), 8.2 (d, 1 H), 7.9
(s, 1 H), 7.65 (m, 1H), 7.05 (s, 1 H), 6.75 (d, 1 H), 6.7 (m, 2 H),
6.6 (m, 1 H), 6.3 (m, 1 H), 5.9 (s, 2 H), 4.0 (m, 3 H), 3.3 (m, 4 H).
Anal. (C26H25N8O3F‚0.5H2O) C, H, N.
N-[(1,3-Benzodioxol-5-yl)methyl]-1-[2-(1H-imidazol-1-yl)py-
rimidin-4-yl]-4-(2-furylmethyl)-2-piperazineacetamide (11u). 1H
NMR (DMSO-d6) δ 8.45 (s, 1 H), 8.35 (br, 1 H), 8.15 (d, 1 H),
7.8 (s, 1 H), 7.0 (s, 1 H), 6.6 (m, 4 H), 5.85 (s, 2 H), 4.0 (m, 5 H),
3.3 (m, 2 H), 3.2 (q, 2 H), 2.9 (d, 1 H), 2.8 (d, 1 H), 2.6 (m, 2H),
2.4 (d, 1 H), 2.25 (m, 1 H), 1.15 (t, 3 H). Anal. (C25H29N7O5‚
0.4H2O) C, H, N.
N-[(4-Fluorophenyl)methyl]-1-[2-(1H-imidazol-1-yl)pyrimidin-
1
4-yl]-2-piperidineacetamide (12i). H NMR (CDCl3) δ 8.4 (s, 1
H), 8.05 (d, 1 H), 7.75 (s, 1 H), 7.0 (m, 3 H), 6.8 (m, 2 H), 6.7 (m,
1 H), 6.5 (m, 1 H), 5.1 (br, 1 H), 4.25 (m, 3 H), 3.0 (m, 1 H), 2.7
(dd, 1 H), 2.55 (dd, 1 H), 1.3-1.8 (m, 6 H). Anal. (C21H23N6OF‚
0.8H2O) C, H, N.
1-[2-(1H-Imidazol-1-yl)-4-pyrimidinyl]-N-[[4-(trifluorometh-
oxy)phenyl]methyl]-2-piperidineacetamide (12j). 1H NMR (CDCl3)
δ 8.5 (s, 1 H), 8.1 (d, 1 H), 7.8 (s, 1 H), 7.1 (m, 4 H), 6.5 (d, 1 H),
6.4 (br s, 1 H), 5.2 (br s, 1 H), 4.3 (m, 2 H), 3.0 (m, 1 H), 2.6 (m,
2 H), 1.8 (m, 6 H, partially obscured by water), 1.6 (m, 1 H). Anal.
(C22H23F3N6O2‚H2O) C, H, N.
1-[2-(1H-Imidazol-1-yl)pyrimidin-4-yl]-N-[(4-methylphenyl)-
methyl]-2-piperidineacetamide (12k). 1H NMR (CDCl3) δ 8.4 (s,
1 H), 8.03 (d, 1 H), 7.75 (s, 1 H), 6.95 (m, 5 H), 6.8 (s, 1 H), 6.45
(s, 1 H), 5.0 (br, 1 H), 4.25 (m, 3 H), 2.9 (m, 1 H), 2.6 (m, 1 H),
2.5 (m, 1 H), 2.2 (s, 3 H), 1.3-1.8 (m, 6 H). Anal. (C23H28N6O3‚
H2O‚0.6H2O) C, H, N.
N-[(1,3-Benzodioxol-5-yl)methyl]-1-[2-(1H-imidazol-1-yl)py-
rimidin-4-yl]-4-(1-iminoethyl)-2-piperazineacetamide, Hydro-
chloride (11v). 1H NMR (DMSO-d6) δ 9.5 (m, 1 H), 8.9 (s, 1 H),
8.6 (m, 2 H), 8.25 (m, 1 H), 7.9 (m, 1 H), 7.05 (s, 1 H), 6.7 (m, 4
H), 5.9 (s, 2 H), 4.1 (m, 2 H), 4.0 (m, 3 H), 3.1-3.8 (m, 4 H), 2.6
(m, 2 H), 2.35 and 2.25 (2s, 3 H). MS m/z 463 (M + 1). Anal.
(C23H26N8O3‚H2O) C, H, N.
N-[(1,3-Benzodioxol-5-yl)methyl]-4-[(5-dimethylaminonaph-
thyl)sulfonyl]-1-[2-(1H-imidazol-1-yl)pyrimidin-4-yl]-2-pipera-
1
zineacetamide (11w). H NMR (CDCl3) δ 8.6 (d, 1 H), 8.5 (s, 1
H), 8.3 (d, 1 H), 8.2 (d, 1 H), 8.1 (d, 1 H), 7.8 (s, 1 H), 7.6 (m, 2
H), 7.2 (d, 1 H), 7.1 (s, 1 H), 6.8 (m, 3 H), 6.6 (br s, 1 H), 6.0 (s,
2 H), 4.3 (m, 1 H), 4.2 (m, 1 H), 4.1 (d, 1 H), 3.7 (d, 1 H), 3.2 (br
s, 1 H), 2.9 (s, 6 H), 2.8 (m, 4 H), 2.3 (dd, 1 H). Anal. (C33H34N8O5
S‚CH2Cl2) C, H, N.
N-[(4-Aminophenyl)methyl]-1-[2-(1H-imidazol-1-yl)-4-pyrim-
1
idinyl]-2-piperidineacetamide (12l). H NMR (CDCl3) δ 8.4 (s,
1 H), 8.1 (d, 1 H), 7.7 (s, 1 H), 7.0 (s, 1 H), 6.8 (d, 2 H), 6.5 (m,
3 H), 6.0 (br s, 1 H), 5.1 (s, 1 H), 4.2 (m, 2 H), 2.9 (m, 1 H), 2.6
(m, 2 H), 1.7 (m, 6 H), 1.5 (m, 1 H). Anal. (C21H25N7O‚CH2Cl2)
C, H, N.
N-[(1,3-Benzodioxol-5-yl)methyl]-1-[2-(1H-imidazol-1-yl)-4-
1
pyrimidinyl]-2-piperidineacetamide (12a). H NMR (CDCl3) δ
8.45 (s, 1 H), 8.1 (d, 1 H), 7.85 (s, 1 H), 7.05 (s, 1 H), 6.7 (s, 1 H),
6.5 (m, 4 H), 5.85 (m, 2 H), 5.1 (br, 1 H), 4.2 (m, 3 H), 3.0 (m, 1
H), 2.7 (dd, 1 H), 2.55 (dd, 1 H), 1.6-1.8 (m, 5 H), 1.5 (m, 1 H).
Anal. (C22H24N6O3‚0.7CH2Cl2) C, H, N.
1-[2-(1H-Imidazol-1-yl)-4-pyrimidinyl]-N-[[4-(methylsulfonyl-
1
amino)phenyl]methyl]-2-piperidineacetamide (12m). H NMR
(DMSO-d6) δ 9.6 (s, 1 H), 8.5 (s, 1 H), 8.4 (m, 1 H), 8.1 (d, 1 H),
7.8 (s, 1 H), 7.1 (m, 5 H), 6.7 (m, 1 H), 4.2 (m, 1 H), 4.1 (m, 1 H),
3.0 (br s, 1 H), 2.9 (s, 3 H), 2.5 (m, 4 H, partially obscured by
DMSO), 1.7 (m, 5 H), 1.4 (m, 1 H). Anal. (C22H27N7O3S‚CH2Cl2)
C, H, N.
N-[(4-Dimethylaminophenyl)methyl]-1-[2-(1H-imidazol-1-yl)-
pyrimidin-4-yl]-2-piperidineacetamide (12n). 1H NMR (CDCl3)
δ 8.5 (s, 1 H), 8.1 (d, 1 H), 7.8 (s, 1 H), 7.1 (s, 1 H), 7.0 (d, 2 H),
6.5 (d, 2 H), 6.1 (s, 1 H), 5.1 (br s, 1 H), 4.2 (m, 2 H), 2.9 (m, 1
H), 2.8 (s, 6 H), 2.6 (m, 1 H), 2.5 (m, 1 H), 2.0 (s, 1 H), 1.8 (m,
5 H), 1.5 (m, 1 H). Anal. (C23H29N7O‚CH2Cl2) C, H, N.
1-[2-(1H-Imidazol-1-yl)-4-pyrimidinyl]-N-[[4-(trifluorometh-
yl)phenyl]methyl]-2-piperidineacetamide (12o). 1H NMR (CDCl3)
δ 8.4 (s, 1 H), 8.1 (d, 1 H), 7.8 (s, 1 H), 7.5 (br s, 1 H), 7.4 (d, 2
H), 7.2 (d, 2 H), 7.0 (s, 1 H), 6.5 (s, 1 H), 5.1 (br s, 1 H), 4.4 (m,
2 H), 3.0 (m, 1 H), 2.6 (m, 2 H), 2.5 (br s, 1 H), 1.7 (m, 5 H), 1.5
(m, 1 H). Anal. (C22H23F3N6O‚CH2Cl2) C, H, N.
1-[2-(1H-Imidazol-1-yl)-4-pyrimidinyl]-N-[(4-methoxyphenyl-
)methyl]-2-piperidineacetamide (12b). 1H NMR (CDCl3) δ 8.45
(s, 1 H), 8.1 (d, 1 H), 7.75 (s, 1 H), 7.1 (s, 1 H), 7.0 (d, 2 H), 6.7
(d, 2 H), 6.5 (s, 1 H), 6.25 (m, 1 H), 5.1 (br, 1 H), 4.25 (m, 3 H),
3.75 (s, 3 H), 2.59 (m, 1 H), 2.65 (dd, 1 H), 2.55 (dd, 1 H), 1.3-
1.8 (m, 6 H). Anal. (C22H26N6O2‚0.8H2O) C, H, N.
1-[2-(1H-Imidazol-1-yl)pyrimidin-4-yl]-N-[(3-methoxyphenyl-
1
)methyl]-2-piperidineacetamide (12c). H NMR (CDCl3) δ 8.4
(s, 1 H), 8.0 (m, 1 H), 7.75 (s, 1 H), 7.3 (m, 1 H), 7.05 (t, 1 H),
6.95 (s, 1 H), 6.6 (m, 3 H), 6.6 (m, 1 H), 5.0 (br, 1 H), 4.25 (m, 3
H), 3.65 (s, 3 H), 2.9 (m, 3 H), 2.6 (m, 2 H), 1.3-1.8 (m, 6 H).
Anal. (C22H26N6O2‚0.3H2O) C, H, N.
1-[2-(1H-Imidazol-1-yl)pyrimidin-4-yl]-N-[(2-methoxyphenyl-
1
)methyl]-2-piperidineacetamide (12d). H NMR (CDCl3) δ 8.4
(s, 1 H), 8.0 (d, 1 H), 7.8 (s, 1 H), 7.1 (m, 2 H), 6.7 (m, 2 H), 6.4
(d, 1 H), 6.3 (m, 1 H), 5.0 (br s, 1H), 4.3 (m, 2 H), 3.8 (s, 3 H), 2.9
(m, 1 H), 2.8 (m, 2 H), 2.0 (m, 1 H), 1.7 (m, 5 H), 1.5 (m, 1 H).
Anal. (C22H26N6O2‚H2O) C, H, N.
N-[(4-Cyanophenyl)methyl]-1-[2-(1H-imidazol-1-yl)pyrimidin-
1
4-yl]-2-piperidineacetamide (12p). H NMR (CDCl3) δ 8.4 (s, 1
H), 8.1 (d, 1 H), 7.8 (s, 1 H), 7.4 (d, 2 H), 7.2 (d, 2 H), 7.0 (s, 1
H), 6.8 (m, 1 H), 6.5 (m, 1 H), 5.2 (br s, 1 H), 4.4 (m, 2 H), 3.0
(m, 1 H), 2.8 (dd, 1 H), 2.6 (dd, 1 H), 1.8 (m, 5 H), 1.6 (m, 1 H).
Anal. (C22H23N7O‚CH2Cl2) C, H, N.
1-[2-(1H-Imidazol-1-yl)pyrimidin-4-yl]-N-[(3,4-dimethoxyphe-
1
nyl)methyl]-2-piperidineacetamide (12e). H NMR (DMSO-d6)
δ 8.5 (s, 1 H), 8.4 (m, 1 H), 8.15 (d, 1 H), 7.85 (s, 1 H), 7.05 (s,
1 H), 6.7 (m, 3 H), 6.6 (d, 1 H), 4.1 (m, 2 H), 3.6 (2 s, 6 H), 3.1
(m, 1 H), 3.0 (m, 2 H), 1.3-1.8 (m, 6 H). Anal. (C23H28N6O3‚
H2O) C, H, N.
1-[2-(1H-Imidazol-1-yl)pyrimidin-4-yl]-N-[(4-nitrophenyl)-
methyl]-2-piperidineacetamide (12q). 1H NMR (CDCl3) δ 8.4 (s,
1 H), 8.1 (d, 1 H), 8.0 (d, 2 H), 7.8 (s, 1 H), 7.2 (d, 2H), 7.1 (s, 1
H), 6.5 (d, 1 H), 5.2 (br s, 1H), 4.5 (dd, 1 H), 4.3 (dd, 1 H), 3.1
(m, 1 H), 2.8 (dd, 1 H), 2.6 (dd, 1 H), 1.8 (m, 4 H), 1.6 (m, 3 H,
partially obscured by water). Anal. (C21H23N7O3‚CH2Cl2) C, H, N.
N-[(4-Aminosulfonylphenyl)methyl]-1-[2-(1H-imidazol-1-yl)-
pyrimidin-4-yl]-2-piperidineacetamide (12r). 1H NMR (DMSO-
d6) δ 8.6 (s, 2 H), 8.2 (d, 1 H), 7.8 (s, 1 H), 7.7 (d, 2 H), 7.3 (m,
4 H), 7.1 (s, 1 H), 6.7 (d, 1 H), 4.2 (m, 2 H), 3.0 (m, 1 H), 2.5 (m,
3 H, partially obscured by DMSO), 2.3 (m, 1 H), 1.6 (m, 5 H), 1.4
(m, 1 H). Anal. (C21H25N7O3) C, H, N.
1-[2-(1H-Imidazol-1-yl)pyrimidin-4-yl]-N-[(3,4,5-trimethoxy-
1
phenyl)methyl]-2-piperidineacetamide (12f). H NMR (CDCl3)
δ 8.5 (s, 1 H), 8.1 (d, 1 H), 7.8 (s, 1 H), 7.1 (s, 1 H), 6.5 (m, 1 H),
6.3 (s, 2 H), 6.2 (br, 1 H), 5.15 (br, 1 H), 4.4 (dd, 1 H), 4.2 (m, 1
H), 3.82 (s, 3 H), 3.77 (s, 6 H), 3.0 (m, 1 H), 2.7 (dd, 1 H), 2.55
(dd, 1 H), 1.3-1.8 (m, 6 H). Anal. (C24H30N6O4) C, H, N.
1-[2-(1H-Imidazol-1-yl)pyrimidin-4-yl]-N-(phenylmethyl)-2-
piperidineacetamide (12g). 1H NMR (CDCl3) δ 8.4 (s, 1 H), 8.05
(d, 1 H), 7.75 (s, 1 H), 7.0-7.3 (m, 6 H), 6.7 (br, 1 H), 6.5 (m, 1