Reaction #78006

Reaction equation

{3-[5-Methyl-3-(2-(N-ethyl-N-(4-pyridylmethyl)aminosulfonyl)phenylsulfonyloxy) phenoxy]propoxy}guanidine dihydrochloride

α-cyano-4-hydroxycinnamic acid

→

title compound

Yield 84.0%

3-[5-Methyl-3-(2-(5-ethyl-N-(4-pyridylmethyl)aminosulfonyl)phenylsulfonyloxy) phenoxy]propoxyguanidine Dihydrochloride

Yield 84.0%

Conditions

Workup

1. 1
   Otheras prepared in the preceding step, in a manner analogous to step i of Example 20

Procedure

{3-[5-Methyl-3-(2-(N-ethyl-N-(4-pyridylmethyl)aminosulfonyl)phenylsulfonyloxy) phenoxy]propoxy}guanidine dihydrochloride: The title compound was prepared in 84% yield from N,N′-(Bis-tert-butyloxycarbonyl)-{3-[5-methyl-3-(2-(N-ethyl-N-(4-pyridylmethyl)aminosulfonyl)phenylsulfonyloxy) phenoxy]propoxy}guanidine, as prepared in the preceding step, in a manner analogous to step i of Example 20. 1H-NMR (300 MHz, DMSO-d6) δ 8.54 (d, J=4.5 Hz, 2H), 8.23 (d, J=7.9 Hz, 1H), 8.17 (d, J=7.8 Hz, 1H), 8.01 (t, J=7.7 Hz, 1H), 7.89 (t, J=7.7 Hz, 1H), 7.42 (br s, 4H), 7.34 (d, J=5.8 Hz, 2H), 6.74 (s, 1H), 6.54 (s, 1H), 6.50 (s, 1H), 4.67 (s, 2H), 3.97 (t, J=6.3 Hz, 2H), 3.87 (t, J=6.3 Hz, 2H), 3.36 (t, J=7.1 Hz, 2H), 2.21 (s, 3H), 2.00 (pentet, J=6.1 Hz, 2H), 0.92 (t, J=7.1 Hz, 3H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C25H31N5O7S2: 578.2 (M+H), 600.2 (M+Na), 616.1 (M+K). Found: 578.1, 599.9, 616.0.

Source