ACCEPTED MANUSCRIPT
4
.1.5.8. R/S-1-[1-(5-bromo-2-ethoxyphenyl)ethyl]-3-(4-methylphenyl)sulfonylurea (A8)
The title compound was obtained as described for A1, starting from amine 6b (1 g, 4.1 mmol)
and 4-methylbenzenesulfonyl isocyanate (0.75 mL, 4.92 mmol). White solid (1.41 g, 78%).
+
+ 1
m.p. 184-185°C. SM (ESI): m/z 441-443 [M+H] , 463-465 [M+Na] . H NMR (δ ppm):
1
2
8
.24 (d, J = 6.8 Hz, 3H, CHCH ), 1.32 (m, 3H, OCH CH ), 2.38 (s, 3H, PhCH ), 4.03 (m,
3
2
3
3
H, OCH CH ), 4.86 (m, 1H, NHCHCH ), 6.93 (d, J
= 8.6 Hz, 1H, CHar), 6.99 (d, J =
2
3
3
ortho
.3 Hz, 1H, NHCH), 7.29 (d, Jmeta = 2.5 Hz, 1H, CHar), 7.36 (dd, Jortho = 8.6 Hz, Jmeta = 2.5
Hz, 1H, CHar), 7.39 (d, Jortho = 8.3 Hz, 2H, CHar), 7.77 (d, Jortho = 8.3 Hz, 2H, CHar), 10.61
13
(
br s, 1H, SO NH). C NMR (δ ppm): 14.4, 21.0, 44.8, 63.7, 111.8, 114.1, 127.1, 128.8,
2
1
4
4
29.4, 130.5, 134.3, 137.3, 143.6, 150.4, 154.6. Anal. Calcd for C H BrN O S: C, 48.99, H,
18 21 2 4
.80, N, 6.35, found: C, 49.08, H, 4.85, N, 6.50.
.1.5.9. R/S-1-[1-(5-bromo-2-ethoxyphenyl)ethyl]-3-(4-chlorophenyl)sulfonylurea (A9)
The title compound was obtained as described for A1, starting from amine 6b (1 g, 4.1 mmol)
and 4-chlorobenzenesulfonyl isocyanate (0.73 mL, 4.92 mmol). White solid (1.33 g, 70%).
+
+ 1
m.p. 190-191°C. SM (ESI): m/z 461-463-465 [M+H] , 483-485-487 [M+Na] . H NMR (δ
ppm): 1.27 (d, J = 6.8 Hz, 3H, CHCH ), 1.32 (m, 3H, OCH CH ), 4.03 (m, 2H, OCH CH ),
3
2
3
2
3
4
.86 (m, 1H, NHCHCH ), 6.92 (d, J
= 8.6 Hz, 1H, CHar), 7.07 (d, J = 8.1 Hz, 1H,
3
ortho
NHCH), 7.29 (d, Jmeta = 2.5 Hz, 1H, CHar), 7.36 (dd, Jortho = 8.6 Hz, Jmeta = 2.5 Hz, 1H,
13
CHar), 7.68 (m, 2H, CHar), 7.90 (m, 2H, CHar), 10.79 (s, 1H, SO NH). C NMR (δ ppm):
2
1
1
3
4.4, 20.9, 44.7, 63.8, 111.8, 114.1, 128.7, 129.1, 129.2, 130.5, 134.2, 138.1, 138.9, 150.3,
54.5. Anal. Calcd for C H BrClN O S: C, 44.22, H, 3.93, N, 6.07, found: C, 44.18, H,
17
18
2
4
.88, N, 6.12.
4
.1.5.10. R/S-1-[1-(5-bromo-2-isopropoxyphenyl)ethyl]-3-phenylsulfonylurea (A10)
The title compound was obtained as described for A1, starting from amine 6c (1 g, 3.87
mmol) and benzenesulfonyl isocyanate (0.62 mL, 4.64 mmol). White solid (1.13 g, 66%).
+
+ 1
m.p. 180-181°C. SM (ESI): m/z 441-443 [M+H] , 463-465 [M+Na] . H NMR (δ ppm):
1
.23 (d, J = 6.0 Hz, 3H, CHCH ), 1.26 (d, J = 6.3 Hz, 6H, OCH(CH ) ), 4.63 (sept, J = 6.3
3 3 2
Hz, 1H, OCH(CH ) ), 4.86 (m, 1H, NHCHCH ), 6.96 (d, J = 8.9 Hz, 1H, CHar), 6.98 (d,
ortho
3
2
3
J = 8.2 Hz, 1H, NHCH), 7.30 (d, Jmeta = 2.6 Hz, 1H, CHar), 7.35 (dd, Jortho = 8.9 Hz, Jmeta
=
2
1
1
4
.6 Hz, 1H, CHar), 7.60 (m, 2H, CHar), 7.69 (m, 1H, CHar), 7.89 (m, 2H, CHar), 10.70 (br s,
13
H, SO NH). C NMR (δ ppm): 20.9, 21.5, 21.6, 44.8, 69.8, 111.5, 115.2, 127.0, 127.3,
2
29.0, 130.5, 133.2, 134.9, 140.1, 150.3, 153.5. Anal. Calcd for C H BrN O S: C, 48.99, H,
1
8
21
2
4
.80, N, 6.35, found: C, 48.73, H, 4.76, N, 6.75.