N-(4-amino-4′-hydroxybiphen-3-yl)-4-methoxybenzamide

 


 N-(4-amino-4′-hydroxybiphen-3-yl)-4-methoxybenzamide







Example 45

N-(4-amino-4′-hydroxybiphen-3-yl)-4-methoxybenzamide (160)

Step 1. (3-Bromophenoxy)(tert-butyl)dimethylsilane (159) Following the same procedure as in Example 19, step 2 (scheme 17) substituting compound 90 for 3-bromophenol 158 (200 mg, 0.501 mmol), the title compound 159 was obtained (14 mg, 5% yield). ¹H NMR: (400 MHz, DMSO-d₆) δ (ppm): 7.21 (t, J=8.0 Hz, 1H), 7.14 (d, J=7.8 Hz, 1H), 7.01 (s, 1H), 6.86 (d, J=8.0 Hz, 1H), 0.95 (d, J=1.0 Hz, 9H), 0.20 (d, J=1.2 Hz, 6H).
Step 2. N-(4-amino-4′-hydroxybiphen-3-yl)-4-methoxybenzamide (160) Following the same procedure as in Example 31, step 1 (scheme 21) but substituting 1-(4-bromophenyl)ethanone for compound 159 (312 mg, 1.09 mmol), the title compound 160 was obtained (79 mg, 44% yield).

 ¹H NMR: (400 MHz, DMSO-d₆) δ (ppm): 9.58 (s, 1H), 9.35 (s, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.43 (s, 1H), 7.23 (dd, J=8.2, 1.4 Hz, 1H), 7.16 (t, J=7.6 Hz, 1H), 7.04 (d, J=8.4 Hz, 2H), 6.95 (d, J=7.6 Hz, 1H), 6.91 (s, 1H), 6.82 (d, J=8.4 Hz, 1H), 6.62 (dt, J=8.0, 1.0 Hz, 1H), 5.05 (s, 2H), 3.84 (s, 3H).
LRMS: (m/z): 335.2 (MH⁺).



 SEE



http://www.google.com/patents/US7868205