M. E. Gonzaꢀlez-Rosende et al. / Tetrahedron 63 (2007) 8709–8714
8713
d, J¼5.2); 6.82 (2H, br); 6.92 (1H, br); 7.28 (2H, d, J¼8.1);
7.63 (2H, d, J¼8.1); 7.94 (1H, br) ppm. 13C NMR (75 MHz,
DMSO-d6) d: 11.3 (CH3); 20.8 (CH3); 22.3 (CH2); 40.3
(CH2); 43.3 (CH2NH); 125.6 (CH); 129.0 (CH); 141.1 (C);
141.5 (C); 156.5 (C]N); 168.0 (C]O) ppm. HRMS
(EI+): m/z calcd for C13H20N4O3S 312.1256; found
312.1265. Anal. Calcd for C13H20N4O3S: C, 49.98; H,
6.40; N, 17.92; S, 10.26. Found: C, 50.06; H, 6.57; N,
17.92; S, 10.25.
(C]N); 161.6 (C); 168.2 (C]O) ppm. HRMS (EI+): m/z
calcd for C12H19N4O4S 315.1127; found 315.1125.
3.4.12. N,N-Dimethyl-2-(2-tosylguanidino)acetamide
4Ac. Eluent: EtOAc/MeOH (9:1). Mp: 192–194 ꢀC. 1H
NMR (300 MHz, DMSO-d6) d: 2.33 (3H, s); 2.84 (3H, s);
2.89 (3H, s); 3.93 (2H, d, J¼4.1); 6.90 (2H, br); 7.28 (2H,
d, J¼8.2); 7.44 (1H, br); 7.64 (2H, d, J¼8.2) ppm. 13C
NMR (75 MHz, DMSO-d6) d: 35.4 (CH3); 35.8 (CH3);
42.4 (CH2NH); 126.0 (CH); 129.3 (CH); 141.5 (C); 142.6
(C); 156.7 (C]N); 168.0 (C]O) ppm. HRMS (FAB+):
m/z calcd for C12H19N4O3S 299.1177; found 299.1181.
3.4.7. 2-[2-(4-Bromobenzenesulfonyl)guanidino]-N-pro-
pylacetamide 4Ba. Eluent: hexane/EtOAc (1:4). Mp: 202–
1
205 ꢀC. H NMR (300 MHz, DMSO-d6) d: 0.85 (3H, t,
J¼7.1); 1.40 (2H, sextet, J¼7.1); 3.04 (2H, q, J¼6.7); 3.76
(2H, d, J¼5.2); 6.91 (2H, br); 7.05 (1H, br); 7.72 (4H, s);
7.97 (1H, t, J¼5.2) ppm. 13C NMR (75 MHz, DMSO-d6)
d: 11.7 (CH3); 22.6 (CH2); 40.7 (CH2); 43.7 (CH2NH);
125.1 (C); 128.1 (CH); 132.0 (CH); 143.9 (C); 157.0
(C]N); 168.3 (C]O) ppm. HRMS (EI+): m/z calcd for
C12H17N4O3SBr 376.0204; found 376.0199.
3.4.13. 2-[2-(4-Bromobenzenesulfonyl)guanidino]-N,N-
dimethylacetamide 4Bc. Eluent: EtOAc/MeOH (9:1). Oil.
1H NMR (300 MHz, DMSO-d6) d: 2.81 (3H, s); 2.95 (3H,
s); 3.95 (2H, d, J¼5.2); 6.88 (2H, br); 7.0 (1H, br); 7.75
(4H, s) ppm. 13C NMR (75 MHz, DMSO-d6) d: 35.4
(CH3); 35.9 (CH3); 42.5 (CH2NH); 125.1 (C); 125.1 (CH);
128.2 (CH); 143.8 (C); 156.3 (C]N); 168.1 (C]O) ppm.
HRMS (EI+): m/z calcd for C11H15BrN4O3S 362.0048;
found 362.0013.
3.4.8. 2-[2-(4-Methoxybenzenesulfonyl)guanidino]-N-
propylacetamide 4Ca. Eluent: EtOAc/MeOH (9:1). Mp:
1
147–149 ꢀC. H NMR (300 MHz, DMSO-d6) d: 0.82 (3H,
3.4.14. 2-(4-Nitrophenylamino)-N-propylacetamide 5.
1
t, J¼7.1); 1.38 (2H, sextet, J¼7.1); 3.01 (2H, q, J¼7.1);
3.72 (2H, d, J¼5.2); 3.80 (3H, s); 6.82 (2H, br); 6.92 (1H,
br); 6.99 (2H, d, J¼8.6); 7.68 (2H, d, J¼8.6); 7.94 (1H, t,
J¼5.2) ppm. 13C NMR (75 MHz, DMSO-d6) d: 11.7
(CH3); 22.6 (CH2); 40.7 (CH2); 43.7 (CH2NH); 55.8
(OCH3); 114.0 (CH); 127.9 (CH); 136.7 (C); 156.6
(C]N); 161.6 (C); 168.2 (C]O) ppm. HRMS (EI+): m/z
calcd for C13H20N4O4S 328.1205; found 328.1219.
Eluent: hexane/EtOAc (3:7). Mp: 140–142 ꢀC. H NMR
(300 MHz, DMSO-d6) d: 0.80 (3H, t, J¼7.35); 1.40 (2H,
sextet, J¼7.35); 3.04 (2H, q, J¼7.35); 3.82 (2H, d, J¼6);
6.63 (2H, d, J¼9.4); 7.49 (1H, t, J¼6); 7.99 (2H, d, J¼9);
8.10 (1H, t, J¼4) ppm. 13C NMR (75 MHz, DMSO-d6) d:
11.6 (CH3); 22.7 (CH2); 40.7 (CH2); 46.0 (CH2NH); 111.5
(CH); 126.3 (CH); 136.5 (C); 154.7 (C); 168.8 (C]O)
ppm. HRMS (EI+): m/z calcd for C11H16N3O3 238.1191;
found 238.1251.
3.4.9. N-Ethyl-2-(2-tosylguanidino)acetamide 4Ab. Elu-
ent: EtOAc/MeOH (9:1). Mp: 158–160 ꢀC. 1H NMR
(300 MHz, DMSO-d6) d: 0.99 (3H, t, J¼7.1); 2.33 (3H, s);
3.08 (2H, quintet, J¼7.1); 3.71 (2H, d, J¼5.2); 6.85 (2H,
br); 6.97 (1H, br); 7.27 (2H, d, J¼8.0); 7.64 (2H, d,
J¼8.0); 7.95 (1H, t, J¼5.2) ppm. 13C NMR (75 MHz,
DMSO-d6) d: 15.0 (CH3); 21.2 (CH3); 33.8 (CH2); 43.7
(CH2NH); 126.0 (CH); 129.3 (CH); 141.5 (C); 141.9 (C);
157.0 (C]N); 168.2 (C]O) ppm. HRMS (EI+): m/z calcd
for C12H18N4O3S; 298.1099; found 298.1069.
Acknowledgements
ꢀ
We are indebted to the Ministerio de Ciencia y Tecnologıa
(Project BQU2003-01756) and Generalitat Valenciana (Pro-
ject GV05/139) for financial support. The authors are grate-
ful to Dr. Luis Domingo (University of Valencia) for his
helpful suggestions.
References and notes
3.4.10. 2-[2-(4-Bromobenzenesulfonyl)guanidino]-N-
ethylacetamide 4Bb. Eluent: EtOAc. Mp: 110–114 ꢀC.
1H NMR (300 MHz, DMSO-d6) d: 0.98 (3H, t, J¼7.1);
3.07 (2H, quintet, J¼7.1); 3.70 (2H, d, J¼5.2); 6.87
(2H, br); 7.01 (1H, br); 7.69 (4H, s); 7.95 (1H, t, J¼5.2)
ppm. 13C NMR (75 MHz, DMSO-d6) d: 15.0 (CH3); 33.8
(CH2); 43.7 (CH2NH); 125.1 (C); 128.1 (CH); 132.0 (CH);
143.9 (C); 157.0 (C]N); 168.2 (C]O) ppm. HRMS
(EI+): m/z calcd for C11H16N4O3SBr 363.0126; found
363.0130.
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1. Lasri, J.; Gonzalez-Rosende, M. E.; Sepulveda-Arques, J.
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3.4.11. N-Ethyl-2-[2-(4-methoxybenzenesulfonyl)guani-
dino]acetamide 4Cb. Eluent: EtOAc/MeOH (9:1). Mp:
1
136–139 ꢀC. H NMR (300 MHz, DMSO-d6) d: 0.99 (3H,
t, J¼7.1); 3.07 (2H, quintet, J¼7.1); 3.69 (2H, d, J¼5.2);
3.8 (3H, s); 6.82 (3H, br); 6.99 (2H, d, J¼9.0); 7.68 (2H,
d, J¼9.0); 7.95 (1H, br) ppm. 13C NMR (75 MHz, DMSO-
d6) d: 14.9 (CH3); 33.8 (CH2); 43.7 (CH2NH); 55.8
(OCH3); 114.0 (CH); 127.9 (CH); 136.7 (C); 156.8
4. Todorova, T.; Linden, A.; Heimgartner, H. Helv. Chim. Acta
1999, 82, 354.