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5.1.1.15. 1-(3-Benzoyl-imidazolidin-1-yl)ethanone 1224. Oil. (1H)
NMR (CDCl3) d: 2.09 (s, 3H, COCH3); 3.69–3.75 (m, 3H) and 4.08
(br s, 1H) (CH2N); 4.92 (br s, 1H) and 5.16 (br s, 1H) (NCH2N);
7.40–7.50 (m, 5H, aromatic protons) ppm. (13C) NMR (CDCl3) d:
21.99, 22.33, 37.40, 44.50, 63.15, 127.21, 128.64, 130.93, 135.14,
168.40 ppm.
5.1.1.22. 1-[3-(Propane-2-sulfonyl)tetrahydropyrimidin-1-yl]-
ethanone 19. Oil. 1H NMR (CDCl3) d: 1.32–1.36 (m, 6H, CH(CH3)2);
1.72–1.78 (m, 2H, CH2CH2CH2); 2.10 (s, 38%) and 2.24 (s, 62%) (3H,
–COCH3); 3.13–3.20 (m, 62%) and 3.29–3.34 (m, 38%) (1H, CHMe2);
3.55–3.74 (m, 4H, CH2N); 4.89 (s, 62%) and 4.95 (s, 38%) (2H,
NCH2N) ppm. 13C NMR (CDCl3) d: 16.58, 20.67, 41.08, 46.40,
54.20, 61.14, 168.45 ppm. Anal. Calcd for C9H18N2O3S: C, 46.13;
H, 7.74; N, 11.96. Found: C, 46.54; H, 7.65; N, 11.76.
5.1.1.16. 1-[3-(Propane-2-sulfonyl)imidazolidin-1-yl]ethanone
13. Oil. 1H NMR (CDCl3) d: 1.39–1.42 (m, 6H, CH(CH3)2); 2.09–2.10
(m, 3H, COCH3); 3.25 (sept., 1H, J = 6.8 Hz, CHMe2); 3.62 (t, 2H,
J = 6.8 Hz, CH2N); 3.79 (t, 2H, J = 6.8 Hz, CH2N); 4.84 (s, 38%) and
4.87 (s, 62%) (2H, NCH2N) ppm. 13C NMR (CDCl3) d: 16.51, 44.34,
45.95, 46.85, 47.95, 54.70, 62.18, 62.42, 167.49, 168.30 ppm. Anal.
Calcd for C8H16N2O3S: C, 43.62; H, 7.32; N, 12.72. Found: C, 43.32;
H, 7.62; N, 12.37.
5.1.1.23. 1-[3-(4-Fluoro-benzenesulfonyl)tetrahydropyrimidin-
1-yl]propan-1-one 20. Mp 87 °C. 1H NMR (CDCl3) d: 1.06 (t,
J = 7.2 Hz, 45%) and 1.19 (t, J = 7.2 Hz, 55%) (3H, CH2CH3); 1.45–
1.47 (m, 45%) and 1.66–1.68 (m, 55%) (2H, CH2CH2CH2); 2.16 (q,
J = 7.2 Hz, 45%) and 2.51 (q, J = 7.2 Hz, 55%) (2H, CH2CH3); 3.29 (t,
J = 5.2 Hz, 55%) and 3.42 (t, J = 5.2 Hz, 45%) (2H, CH2N); 3.54–3.59
(m, 2H, CH2N); 4.73 (s, 55%) and 5.04 (s, 45%) (2H, NCH2N);
7.15–7.28 (m, 2H) and 7.79–7.90 (m, 2H) (aromatic protons)
ppm. 13C NMR (CDCl3) d: 9.06, 9.16, 23.93, 24.07, 26.20, 41.26,
44.31, 45.35, 45.88, 56.14, 60.65, 116.19 (d, J = 22.0 Hz), 116.70
(d, J = 22.0 Hz), 130.01 (d, J = 9.0 Hz), 130.30 (d, J = 9.0 Hz),
132.20, 161.20 (d, J = 250.0 Hz), 162.40 (d, J = 250 Hz), 170.8 ppm.
Anal. Calcd for C13H17FN2O3S: C, 51.99; H, 5.71; N, 9.33. Found:
C, 51.86; H, 5.49; N, 9.54.
5.1.1.17. 1-[3-(4-Fluorobenzenesulfonyl)imidazolidin-1-yl]pro-
pan-1-one 14. Mp 96 °C. 1H NMR (CDCl3) d: 1.05 (t, J = 7.6 Hz, 66%)
and 1.12 (t, J = 7.6 Hz, 34%) (3H, CH2CH3); 2.07 (q, J = 7.6 Hz, 66%)
and 2.20 (q, J = 7.6 Hz, 34%) (2H, CH2CH3); 3.43–3.50 (m, 34%)
and 3.62 (t, J = 6.4 Hz, 66%) (4H, CH2N); 4.69 (s, 34%) and 4.75 (s,
66%) (2H, NCH2N); 7.21–7.28 (m, 2H) and 7.81–7.86 (m, 2H) (aro-
matic protons) ppm. 13C NMR (CDCl3) d: 8.46, 8.68, 27.38, 27.90,
43.54, 44.07, 45.96, 47.43, 61.61, 61.69, 116.70 (d, J = 23.0 Hz),
130.35 (d, J = 9 Hz), 132.26, 165.64 (d, J = 255.0 Hz), 171.46 ppm.
Anal. Calcd for C12H15FN2O3S: C, 50.34; H, 5.28; N, 9.78. Found:
C, 50.40; H, 5.49; N, 9.63.
5.1.1.24. 1-(3-Benzoyl-tetrahydropyrimidin-1-yl)propan-1-one
21. Oil. 1H NMR (CDCl3) d: 1.08–1.26 (m, 3H, CH2CH3); 1.64–1.81 (m,
2H, CH2CH2CH2); 2.31–2.34 (m, 1H, CH2CH3); 2.64–2.66 (m, 1H,
CH2CH3); 3.62–3.78 (m, 4H, CH2N); 5.09–5.23 (m, 2H, NCH2N); 7.42–
7.44 (m, 5H, aromatic protons) ppm. 13C NMR (CDCl3) d: 9.27, 25.32,
26.45, 32.20, 41.57, 44.98, 127.09, 127.49, 128.28, 128.43, 128.63,
129.94, 130.33, 134.77, 170.27 ppm. Anal. Calcd for C14H18N2O2: C,
68.27; H, 7.37; N, 11.37. Found: C, 68.41; H, 7.53; N, 11.60.
5.1.1.18. 1-(3-Benzoylimidazolidin-1-yl)propan-1-one 1524. Mp
78 °C. 1H NMR (CDCl3) d: 1.14–1.24 (m, 3H, CH2CH3); 2.29–2.35
(m, 2H, CH2CH3); 3.50–3.76 (m, 4H, CH2N); 4.93–5.15 (m, 2H,
NCH2N); 7.41–7.55 (m, 5H, aromatic protons) ppm. 13C NMR
(CDCl3) d: 8.68, 8.79, 27.47, 27.89, 42.15, 42.28, 47.50, 47.80,
126.94, 127.05, 127.21, 127.44, 128.48, 128.61, 130.88, 131.49,
135.18, 168.20, 171.68 ppm.
5.1.1.25. 1-[3-(Propane-2-sulfonyl)tetrahydropyrimidin-1-yl]-
propan-1-one 22. Oil. 1H NMR (CDCl3) d: 1.13–1.17 (m, 3H, CH2CH3);
1.31–1.36 (m, 6H, C(CH3)2); 1.74–1.76 (m, 2H, CH2CH2CH2); 2.35–
2.52 (m, 2H, CH2CH3); 3.13–3.28 (m, 1H, CHMe2); 3.45–3.73 (m, 4H,
CH2N); 4.89 (s, 61%) and 4.94 (s, 39%) (2H, NCH2N) ppm. 13C NMR
(CDCl3) d: 9.15, 9.68, 16.56, 25.33, 25.92, 41.21, 42.46, 44.66, 46.39,
50.69, 54.08, 56.54, 60.22, 172.11 ppm. Anal. Calcd for C10H20N2O3S:
C, 48.36; H, 8.12; N, 11.28. Found: C, 48.64; H, 8.46; N, 11.39.
5.1.1.19. 1-[3-(Propane-2-sulfonyl)imidazolidin-1-yl]propan-1-
one 16. Oil. 1H NMR (CDCl3) d: 1.08–1.11 (m, 3H, CH2CH3); 1.31–
1.33 (m, 6H, CH(CH3)2); 2.21–2.26 (m, 2H, CH2CH3); 3.17–3.22
(m, 1H, –CHMe2); 3.55 (t, J = 6.4 Hz, 2H, CH2N); 3.72 (t, J = 6.4 Hz,
2H, CH2N); 4.77 (s, 39%) and 4.80 (s, 61%) (2H, NCH2N) ppm. 13C
NMR (CDCl3) d: 8.58, 8.72, 16.45, 16.94, 27.71, 27.94, 44.09,
45.04, 46.56, 47.87, 54.50, 54.56, 61.61, 61.72, 170.86,
171.54 ppm. Anal. Calcd for C9H18N2O3S: C, 46.13; H, 7.74; N,
11.96. Found: C, 46.37; H, 7.90; N, 11.72.
5.1.1.26. 4-Propionylpiperazine-1-carboxylic acid phenyl ester
23. Oil. 1H NMR (CDCl3) d: 1.20 (t, J = 7.2 Hz, 3H, CH2CH3); 2.40 (q,
J = 7.2 Hz, 2H, CH2CH3); 3.52–3.77 (m, 8H, CH2N); 7.12–7.15 (m,
2H), 7.21–7.26 (m, 1H) and 7.36–7.41 (m, 2H) (aromatic protons)
ppm. 13C NMR (CDCl3) d: 9.40, 26.55, 41.28, 43.94, 44.41, 45.10,
121.63, 125.54, 129.36, 151.13, 153.90, 172.51 ppm. Anal. Calcd
for C14H18N2O3: C, 64.10; H, 6.92; N, 10.68. Found: C, 64.54; H,
6.78; N, 10.89.
5.1.1.20. 1-[3-(4-Fluorobenzenesulfonyl)tetrahydropyrimidin-
1-yl]ethanone 17. Oil. 1H NMR (CDCl3) d: 1.46–1.51 (m, 42%) and
1.63–1.69 (m, 58%) (2H, CH2CH2CH2); 1.95 (s, 42%) and 2.24 (s,
58%) (3H, COCH3); 3.31 (t, J = 5.6 Hz, 58%) and 3.42 (t, J = 5.6 Hz,
42%) (2H, CH2N); 3.52–3.60 (m, 2H, CH2N); 4.74 (s, 58%) and 5.00
(s, 42%) (2H, NCH2N); 7.17–7.28 (m, 2H, aromatic protons); 7.80–
7.82 (m, 58%) and 7.84–7.87 (m, 42%) (2H, aromatic protons) ppm.
13C NMR (CDCl3) d: 20.99, 21.19, 23.87, 24.01, 41.11, 45.18, 45.25,
45.75, 55.96, 61.45, 116.26 (d, J = 23.0 Hz), 116.72 (d, J = 23.0 Hz),
130.00 (d, J = 9 Hz), 130.30 (d, J = 9 Hz), 168.03 (d, J = 290.2 Hz),
168.20 (d, J = 290 Hz) 169.51 ppm. Anal. Calcd for C12H15FN2O3S: C,
50.34; H, 5.28; N, 9.78. Found: C, 50.43; H, 5.57; N, 9.41.
5.1.1.27. 4-Propionylpiperazine-1-carboxylic acid phenylamide
24. Oil. 1H NMR (CDCl3) d: 1.19 (t, J = 7.2 Hz, 3H, CH2CH3); 2.40 (q,
J = 7.2 Hz, 2H, CH2CH3); 3.46–3.77 (m, 8H, CH2N); 6.44 (br s, 1H,
NH); 7.06–7.10 (m, 1H) and 7.28–7.38 (m, 4H) (aromatic protons)
ppm. 13C NMR (CDCl3) d: 9.41, 26.51, 41.11, 43.53, 44.12, 45.08,
120.60, 123.31, 128.77, 139.08, 155.37, 172.64 ppm. Anal. Calcd for
C14H19N3O2: C, 64.35; H, 7.33; N, 16.08. Found: C, 64.54; H, 7.61;
N, 16.41.
5.1.1.21. 1-(3-Benzoyltetrahydropyrimidin-1-yl)ethanone 18. Oil.
1H NMR (CDCl3) d: 1.63–1.82 (m, 3H, COCH3); 2.33–2.36 (m, 2H,
CH2CH2CH2); 3.61–3.78 (m, 4H, CH2N); 5.07–5.21 (m, 2H, NCH2N);
7.43–7.46 (m, 5H, aromatic protons) ppm. 13C NMR (CDCl3) d: 21.34,
25.28, 25.42, 41.43, 45.90, 127.12, 127.48, 128.27, 128.68, 128.78,
130.40, 134.69, 170.37 ppm. Anal. Calcd for C13H16N2O2: C, 67.22; H,
6.94; N, 12.06. Found: C, 66.98; H, 7.12; N, 12.39.
5.1.1.28. 1-(4-Phenylacetylpiperazin-1-yl)propan-1-one 25. Oil.
1H NMR (CDCl3) d: 1.09 (t, J = 7.6 Hz, 3H, CH2CH3); 2.27 (br s, 2H,
CH2CH3); 3.19 (br s, 1H) and 3.37–3.70 (m, 7H) (CH2N); 3.87 (s,
2H, COCH2Ph); 7.17–7.23 (m, 3H) and 7.25–7.31 (m, 2H) (aromatic
protons) ppm. 13C NMR (CDCl3) d: 9.31, 26.39, 41.01, 41.69, 44.94,
45.84, 126.97, 128.50, 128.83, 134.66, 169.73, 172.44 ppm. Anal.