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5.2.7. N-(4-Methoxybenzyl)-2-(3-oxobenzo[d]isothiazol-2(3H)-
yl)acetamide (13)
2H), 7.35–7.42 (m, 1H), 7.54–7.62 (m, 2H), 8.01–8.05 (m, 1H). 13C
NMR (75 MHz, CDCl3): d 13.11, 14.56, 40.98, 42.01, 44.84, 120.45,
123.72, 125.50, 126.91, 132.21, 141.97, 165.90, 165.93. HRMS
(ESI): calcd for C13H16N2O2S (M+Na) 287.0830; found 287.0834.
Yellow solid (24% yield), mp 166–168 °C. 1H NMR (300 MHz,
CDCl3): d 3.68 (s, 3H), 4.39 (d, J = 5.4 Hz, 2H), 4.55 (s, 2H), 6.56 (s,
1H), 6.8 (d, J = 9.1 Hz, 2H), 7.19 (d, J = 9.1 Hz, 2H), 7.42 (t,
J = 7.8 Hz, 1H), 7.65 (m, J = 7.8 Hz, 2H), 8.01(d, J = 8.0 Hz, 1H). 13C
NMR (75 MHz, CDCl3): d 43.39, 47.66, 55.43, 114.21, 120.59,
123.45, 125.89, 126.70, 126.92, 129.25, 132.55, 141.25, 159.16,
5.2.14. (S)-2-(3-Oxobenzo[d]isothiazol-2(3H)-yl)-N-(1-
phenylethyl)acetamide (20)
White solid (76% yield), mp 191–193 °C. 1H NMR (300 MHz,
CDCl3): d 1.46–1.48 (d, J = 6.9 Hz, 3H), 4.51 (s, 2H), 5.07–5.16 (q,
J = 7.1 Hz, 1H), 6.72–6.75 (d, J = 6.97 Hz, 1H), 7.20–7.32 (m, 5H),
7.41–7.46 (m, 1H), 7.56–7.59 (m, 1H), 7.64–7.69 (m, 1H), 8.02–
8.05 (m, 1H). 13C NMR (75 MHz, CDCl3): d 22.14, 48.03, 49.35,
120.67, 123.48, 127.05, 128.86, 132.66, 142.85, 166.30, 166.31.
166.14, 167.00. HRMS (ESI): calcd for
351.0779; found 351.0779.
C17H16N2O3S (M+Na)
5.2.8. N-(4-Fluorobenzyl)-2-(3-oxobenzo[d]isothiazol-2(3H)-
yl)acetamide (14)
Yellow solid (3% yield), mp 191–192 °C, 1H NMR (300 MHz,
CDCl3): d 4.4 (d, 2H), 4.55 (s, 2H), 6.65 (s, 1H), 6.95 (t, 2H), 7.2
(m, 2H), 7.42 (t, 1H), 7.55–7.66 (m, 2H), 8.05 (d, 1H). 13C NMR
(75 MHz, CDCl3): d 43.06, 47.83, 115.59, 115.80, 120.65, 126.01,
126.93, 129.50, 129.58, 132.69, 141.17, 163.55, 166.22, 167.17.
HRMS (ESI): calcd for C16H14FN2O2S (M+H) 317.0760; found
317.0753.
HRMS (ESI): calcd for
313.1002.
C17H17N2O2S (M+H) 313.1011; found
5.2.15. (R)-2-(3-Oxobenzo[d]isothiazol-2(3H)-yl)-N-(1-
phenylethyl)acetamide (21)
White solid (80% yield), mp 197–199 °C. 1H NMR (300 MHz,
CDCl3): d 1.46–1.48 (d, J = 6.9 Hz, 3H), 4.51 (s, 2H), 5.07–5.16 (q,
J = 7.4 Hz, 1H), 6.75–6.78 (d, J = 7.3 Hz, 1H), 7.20–7.32 (m, 5H),
7.41–7.46 (m, 1H), 7.56–7.59 (m, 1H), 7.64–7.69 (m, 1H), 8.02–
8.05 (m, 1H). 13C NMR (75 MHz, CDCl3): d 22.16, 47.99, 49.34,
120.69, 123.52, 127.04, 128.89, 132.67, 142.91, 166.34, 166.35.
5.2.9. (RS)-N-Benzyl-2-(3-oxobenzo[d]isothiazol-2(3H)-
yl)propanamide (15)
White solid (24% yield), mp 148–149 °C. 1H NMR (300 MHz,
CDCl3): d 1.66 (d, J = 7.6 Hz, 3H), 4.37 (dd, J = 13.6, 5.3 Hz, 1H),
4.49 (dd, J = 13.6, 5.3 Hz, 1H), 5.43 (q, J = 6.4 Hz, 1H), 7.05 (s, 1H),
7.19–7.32 (m, 5H), 7.36 (t, J = 7.0 Hz, 1H), 7.55–7.64 (m, 2H), 7.91
(d, J = 6.9 Hz, 1H). 13C NMR (75 MHz, CDCl3): d 16.84, 43.81,
52.59, 120.64, 124.24, 125.80, 126.77, 127.64, 127.74, 128.91,
132.35, 137.93, 141.33, 166.07, 169.77. HRMS (ESI): calcd for
HRMS (ESI): calcd for
313.1000.
C17H17N2O2S (M+H) 313.1011; found
5.2.16. 2-(3-Oxobenzo[d]isothiazol-2(3H)-yl)-N-
phenethylacetamide (22)
White solid (0.17 g, 23% yield), mp 173–174 °C. 1H NMR
(300 MHz, CDCl3): d 2.75–2.82 (t, 2H), 3.43–3.58 (q, 2H), 4.50 (s,
2H), 6.50 (s, 1H), 7.10–8.12 (m, 9H). 13C NMR (75 MHz, CDCl3): d
35.60, 40.90, 47.95, 120.66, 120.69, 123.51, 126.01, 126.05,
126.63, 127.08, 128.68, 128.86, 132.69, 138.58, 141.01, 165.99,
167.17. HRMS (ESI): calcd for C17H17N2O2S (M+H) 313.1011; found
313.1021.
C17H16N2O2S (M+Na) 335.0830; found 335.0824.
5.2.10. N-Benzyl-N-methyl-2-(3-oxobenzo[d]isothiazol-2(3H)-
yl)acetamide (16)
White solid (34% yield). 1H NMR (300 MHz, DMSO-d6): d 3.00 (s,
3H), 4.60–4.77 (m, 4H), 7.19–7.42 (m, 6H), 7.49–7.63 (m, 2H),
7.96–8.06 (m, 1H). 13C NMR (75 MHz, DMSO-d6): d 33.87, 44.52,
50.47, 121.73, 125.30, 125.62, 126.83, 127.15, 127.57, 128.48,
128.77, 137.28, 141.46, 165.08, 166.44. HRMS (ESI): calcd for
5.2.17. 2-(3-Oxobenzo[d]isothiazol-2(3H)-yl)-N-1-
C
17H17N2O2S (M+H) 313.1011; found 313.1013.
adamantylacetamide (23)
Yellow solid (15% yield), mp 204–205 °C. 1H NMR (300 MHz,
DMSO-d6): d 1.80 (s, 6H), 1.93 (s, 6H), 2.0 (s, 3H), 4.4 (s, 2H),
7.30–8.00 (m, 5H). 13C NMR (75 MHz, DMSO-d6): d 28.77, 35.95,
41.07, 45.85, 51.15, 121.65, 123.50, 125.61, 131.88, 141.46,
5.2.11. (RS)-N-Benzyl-N-methyl-2-(3-oxobenzo[d]isothiazol-
2(3H)-yl)propanamide (17)
Yellow oil (20% yield). 1H NMR (300 MHz, CDCl3): d 1.53 (dd,
J = 22.1, 3.7 Hz, 3H), 3.05 (d, J = 14.7 Hz, 3H), 4.5–4.7 (m, 2H), 5.9
(m, 1H), 7.18–7.5 (m, 7H), 7.59–7.64 (m, 2H), 7.9–8.2 (m, 1H).
13C NMR (75 MHz, CDCl3): d 18.07, 34.94, 48.58, 51.59, 120.47,
120.57, 125.48, 126.42, 126.74, 127.26, 127.81, 128.27, 128.89,
129.00, 132.03, 132.13. HRMS (ESI): calcd for C18H19N2O2S (M+H)
327.1167; found 327.1165.
165.27, 165.38. HRMS (ESI): calcd for
343.1480; found 343.1483.
C19H23N2O2S (M+H)
5.2.18. 2-(3-Oxobenzo[d]isothiazol-2(3H)-yl)-N-2-
thiazolylacetamide (24)
Brown solid (0.27 g, 46% yield), mp 218–220 °C. 1H NMR
(300 MHz, DMSO-d6): d 4.8 (s, 2H), 7.22 (d, 1H), 7.41–7.58 (m,
2H), 7.65 (t, 1H), 7.9 (d, 1H), 8.0 (d, 1H), 12.5 (s, 1H). 13C NMR
(75 MHz, DMSO-d6): d 45.35, 113.86, 121.91, 123.26, 125.47,
125.66, 132.11, 137.79, 141.53, 157.55, 165.07, 165.85. HRMS
(ESI): calcd for C12H19N3O2S2 (M+Na) 314.0034; found 314.0025.
5.2.12. N-Benzyl-N-ethyl-2-(3-oxobenzo[d]isothiazol-2(3H)-
yl)acetamide (18)
Colorless oil (58% yield). 1H NMR (300 MHz, CDCl3): d 1.12–1.25
(m, 3H), 3.35–3.50 (m, 2H), 4.60–4.71 (m, 3H), 4.78 (s, 1H), 7.20–
7.41 (m, 6H), 7.49–7.62 (m, 2H), 7.96–8.04 (m, 1H). 13C NMR
(75 MHz, CDCl3): d 13.95, 41.53, 44.82, 48.62, 120.49, 125.54,
126.42, 126.92, 127.75, 127.97, 128.43, 128.85, 129.18, 132.25,
5.2.19. N-(2-Morpholinoethyl)-2-(3-oxobenzo[d]isothiazol-
2(3H)-yl)acetamide (25)
White solid (0.42 g, 37% yield), mp 187–189 °C. 1H NMR
(300 MHz, DMSO-d6): d 2.2–3.4 (m, 4H), 3.2–3.25 (m, 4H), 3.5–
3.6 (t, 4H), 4.82–4.89 (d, 2H), 7.3–8.03 (m, 4H), 8.90–9.00 (t, 1H).
13C NMR (75 MHz, DMSO-d6): d 35.88, 42.65, 53.26, 57.30, 66.14,
125.61, 125.84, 128.38, 131.47, 132.69, 137.25, 167.11, 168.53.
166.07, 166.90. HRMS (ESI): calcd for
327.1167; found 327.1165.
C18H19N2O2S (M+H)
5.2.13. N,N-Diethyl-2-(3-oxobenzo[d]isothiazol-2(3H)-
yl)acetamide (19)
Yellow oil (38% yield). 1H NMR (300 MHz, CDCl3): d 1.15 (t,
J = 6.2 Hz, 3H), 1.26 (t, J = 6.2 Hz, 3H), 3.36–4.44 (m, 4H), 4.70 (s,
HRMS (ESI). calcd for
344.1031.
C15H19N3O3S (M+Na) 344.1045; found