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6.38 (1H, t, J = 1.8), 3.70 (6H, s), 3.49 (3H, s), 2.96 (6H, s). 13C NMR
(75 MHz, CDCl3) d (ppm): 170.44, 159.97, 149.10, 138.21, 133.94,
127.52, 112.64, 106.71, 102.28, 55.37, 40.60, 38.66. ESIMS(+) m/z
315 (M+H), 337 (M+Na), 353 (M+K).
4.2.48. 3,5-Dimethoxy-N-methyl-N-(naphthalen-2-
yl)benzamide (8q)
Method A was used in combination with 3,5-dimethoxybenzoic
acid and N-methyl 2-naphthlamine (91%). 1H NMR (300 MHz,
CDCl3) d (ppm): 7.81–7.12 (3H, m), 7.56 (1H, d, J = 1.8), 7.49–7.46
(2H, m), 7.26 (1H, dd, J = 1.8, 8.7), 6.58 (2H, d, J = 2.4), 6.33 (1H, t,
J = 2.4), 3.61 (3H, s), 3.57 (6H, s). 13C NMR (75 MHz, CDCl3) d
(ppm): 170.50, 160.14, 142.34, 137.71, 133.47, 131.64, 129.20,
127.74, 126.76, 126.34, 125.21, 124.74, 106.83, 102.39, 55.25,
38.66. ESIMS(+) m/z 322 (M+H), 344 (M+Na), 360 (M+K).
4.2.42. N-(3,5-Dihydroxyphenyl)-4-(dimethylamino)benzamide
(8k)
Method A and D were used in combination with 4-(N,N-dimeth-
ylamino)benzoic acid and 3,5-bis(tert-butyldimethylsilyloxy)ani-
line (54%). 1H NMR (300 MHz, (CD3)2SO) d (ppm): 7.88 (2H, d,
J = 8.7), 6.80 (2H, s), 6.78 (2H, d, J = 8.7), 5.98 (1H, s), 3.04 (6H, s).
13C NMR (75 MHz, (CD3)2SO) d (ppm): 165.56, 158.62, 152.78,
141.55, 129.62, 121.93, 111.23, 99.19, 98.29, 40.26. ESIMS(+) m/z
273 (M+H), 295 (M+Na), 311 (M+K).
4.2.49. N-(3,5-Dihydroxyphenyl)-2-naphthamide (8r)
Method A and D were used in combination with 2-naphtoic acid
and 3,5-bis(tert-butyldimethylsilyloxy)aniline (61%). 1H NMR
(300 MHz, CD3OD) d (ppm): 8.51 (1H, s), 8.09–7.99 (4H, m), 7.66
(2H, m), 6.87 (2H, d, J = 2.1), 6.19 (1H, t, J = 2.1). 13C NMR
4.2.43. N-(3,5-Dihydroxyphenyl)-4-(dimethylamino)-N-
methylbenzamide (8l)
(75 MHz, CD3OD)
d (ppm): 167.66, 158.42, 140.06, 134.96,
132.65, 132.32, 128.84, 128.11, 127.85, 127.66, 127.52, 126.59,
123.89, 99.92, 99.11. ESIMS(+) m/z 280 (M+H), 302 (M+Na), 318
(M+K).
Method A and D were used in combination with 4-(N,N-dimeth-
ylamino)benzoic acid and N-methyl-3,5-bis(tert-butyldimethylsi-
lyloxy)aniline (69%). 1H NMR (300 MHz, CD3OD) d (ppm): 7.34
(2H, d, J = 8.7), 6.53 (2H, d, J = 8.7), 6.21 (1H, t, J = 2.4), 6.16 (2H,
d, J = 2.4), 3.42 (3H, s), 2.91 (6H, s). 13C NMR (75 MHz, CD3OD) d
(ppm): 171.82, 158.82, 151.80, 147.14, 130.41, 121.70, 110.33,
105.53, 100.82, 38.92, 38.07. ESIMS(+) m/z 287 (M+H), 309
(M+Na), 325 (M+K).
4.2.50. N-(3,5-Dihydroxyphenyl)-N-methyl-2-naphthamide (8s)
Method A and D were used in combination with 2-naphtoic acid
and N-methyl 3,5-bis(tert-butyldimethylsilyloxy) aniline (32%). 1H
NMR (300 MHz, (CD3)2CO) d (ppm): 8.09 (1H, s), 7.91–7.87 (2H, m),
7.80 (1H, d, J = 8.7), 7.61–7.52 (3H, m), 6.32 (3H, s), 3.51 (3H, s). 13
C
NMR (75 MHz, (CD3)2CO) d (ppm): 170.13, 158.99, 146.69, 134.09,
133.75, 132.54, 128.75, 128.64, 127.71, 127.29, 127.24, 126.56,
125.49, 106.07, 101.35, 37.88. ESIMS(+) m/z 294 (M+H), 316
(M+Na), 332 (M+K).
4.2.44. 4-(Dimethylamino)-N-(4-hydroxyphenyl)benzamide
(8m)
Method A and D were used in combination with 4-(N,N-dimeth-
ylamino)benzoic acid and 4-(tert-butyldimethylsilyloxy)aniline
(81%). 1H NMR (300 MHz, (CD3)2SO) d (ppm): 7.91 (2H, d, J = 8.7),
7.59 (2H, d, J = 8.1), 6.80 (4H, d, J = 8.7), 3.05 (6H, s). 13C NMR
(75 MHz, (CD3)2SO) d (ppm): 165.24, 153.79, 152.70, 131.73,
129.45, 122.60, 121.93, 115.39, 111.29, 40.26. ESIMS(+) m/z 257
(M+H), 279 (M+Na), 295 (M+K).
4.2.51. 3,4-Dihydroxy-N-(4-hydroxyphenyl)benzamide (8t)
Method B and D were used in combination with 3,4-bis(tert-
butyldimethylsilyloxy)benzoic acid and 4-(tert-butyldimethylsilyl-
oxy)aniline (26%). 1H NMR (300 MHz, CD3OD) d (ppm): 7.47 (2H, d,
J = 8.7), 7.45 (1H, d, J = 2.4), 7.22 (1H, dd, J = 2.4, 8.4), 6.91 (1H, d,
J = 8.4), 6.85 (2H, d, J = 8.7). 13C NMR (75 MHz, CD3OD) d (ppm):
167.41, 154.21, 148.94, 145.01, 130.38, 127.38, 126.22, 123.16,
119.54, 114.85, 114.63. ESIMS(+) m/z 246 (M+H), 268 (M+Na),
284 (M+K).
4.2.45. 4-(Dimethylamino)-N-(4-hydroxyphenyl)-N-methylb-
enzamide (8n)
Method C and D was used from TBS protected 8m (51%). 1H
NMR (300 MHz, (CD3)2SO) d (ppm): 7.16 (2H, d, J = 8.7), 6.98 (2H,
d, J = 9.0), 6.70 (2H, d, J = 8.7), 6.52 (2H, d, J = 9.0), 3.13 (3H, s),
2.92 (6H, s). 13C NMR (75 MHz, (CD3)2SO) d (ppm): 169.85,
155.93, 151.21, 137.65, 130.86, 128.53, 122.97, 116.17, 110.76,
40.60, 40.32.
4.2.52. 3,4-Dihydroxy-N-(4-hydroxyphenyl)-N-
methylbenzamide (8u)
Method C and D were used starting from 8t (58%). 1H NMR
(300 MHz, CD3OD) d (ppm): 6.99 (2H, d, J = 8.7), 6.86 (1H, d,
J = 1.8), 6.75 (2H, d, J = 8.7), 6.71–6.61 (2H, m), 3.44 (3H, s). 13C
NMR (75 MHz, CD3OD) d (ppm): 171.87, 156.01, 147.00, 144.33,
136.78, 127.80, 127.01, 121.12, 115.89, 115.44, 113.98, 37.99.
ESIMS(+) m/z 260 (M+H), 282 (M+Na).
4.2.46. 3,5-Dihydroxy-N-(naphthalen-2-yl)benzamide (8o)
Method A and D was used in combination with 3,5-bis(tert-
butyldimethylsilyloxy)benzoic acid and 2-naphthyl amine (43%).
1H NMR (300 MHz, (CD3)2CO) d (ppm): 8.57 (1H, s), 7.94–7.85
(4H, m), 7.52–7.40 (4H, m), 7.05 (2H, d, J = 1.8), 6.63 (1H, t,
J = 1.8). 13C NMR (75 MHz, (CD3)2CO) d (ppm): 166.28, 158.99,
137.90, 137.28, 134.25, 130.86, 128.55, 127.80, 126.62, 125.02,
120.97, 116.88, 106.38, 105.98. ESIMS(+) m/z 280 (M+H), 302
(M+Na), 318 (M+K).
4.2.53. (Z)-Methyl N-(3,5-dihydroxyphenyl)-2-naphthimidate
(8v)
Compound 8v was prepared by O-methylation of 8r; 8r
(200 mg, 0.39 mmol) was stirred with SOCl2 (5 mL) for 3 h, and vol-
atile materials were removed by evaporation under reduced pres-
sure. MeOH (5 mL) was added to the residue and continued the
stirring for 1 h. After evaporation, method D was used to deprotect
TBS group and purified by flash column chromatography (ethyl
acetate only) to obtain a benzanilide (41 mg, 36%). 1H NMR
(300 MHz, (CD3)2SO) d (ppm): 8.59 (1H, s), 8.15–8.02 (4H, m),
7.71–7.67 (2H, m), 6.87 (2H, d, J = 2.1), 6.05 (1H, t, J = 2.1), 3.42
(3H, s). 13C NMR (75 MHz, (CD3)2SO) d (ppm): 207.05, 165.98,
158.79, 141.10, 134.70, 133.10, 132.57, 129.45, 128.39, 128.16,
127.32, 125.07, 99.33, 98.91, 31.22. ESIMS(+) m/z 332 (M+K).
4.2.47. 3,5-Dimethoxy-N-(naphthalen-2-yl)benzamide (8p)
Method A was used in combination with 3,5-dimethoxybenzoic
acid and 2-naphthlamine (87%). 1H NMR (300 MHz, CDCl3) d
(ppm): 8.31 (1H, s), 7.78–7.62 (4H, m), 7.46–7.38 (2H, m), 7.02
(2H, d, J = 2.4), 6.55 (1H, t, J = 2.4), 3.74 (6H, s). 13C NMR
(75 MHz, CDCl3) d (ppm): 137.15, 135.57, 133.86, 130.83, 128.75,
127.80, 127.63, 126.51, 125.19, 120.50, 117.44, 108.20, 107.13,
105.17, 103.91, 55.56. ESIMS(+) m/z 308 (M+H), 330 (M+Na), 346
(M+K).