Reaktion #78008

ord-4b92092835304512bbbcf77a77af6589

Reaktionsgleichung

N#CC(=Cc1ccc(O)cc1)C(=O)O
α-cyano-4-hydroxycinnamic acid
COC(=O)c1ccc(N(C)S(=O)(=O)c2ccccc2S(=O)(=O)Oc2cc(C)cc(OCCCONC(=N)N)c2)cc1.Cl
3-[5-methyl-3-(2-(N-methyl-N-(4-methoxycarbonylphenyl)aminosulfonyl)phenylsulfonyloxy)phenoxy]propoxyguanidine hydrochloride
→
Cc1cc(OCCCONC(=N)N)cc(OS(=O)(=O)c2ccccc2S(=O)(=O)N(C)c2ccc(C(=O)O)cc2)c1
title compound
Ausbeute 84.0%
Cc1cc(OCCCONC(=N)N)cc(OS(=O)(=O)c2ccccc2S(=O)(=O)N(C)c2ccc(C(=O)O)cc2)c1
3-[5-Methyl-3-(2-(N-methyl-N-(4-carboxyphenyl)aminosulfonyl)phenylsulfonyloxy) phenoxy]propoxyguanidine
Ausbeute 84.0%

Edukte

N#CC(=Cc1ccc(O)cc1)C(=O)O
α-cyano-4-hydroxycinnamic acid
COC(=O)c1ccc(N(C)S(=O)(=O)c2ccccc2S(=O)(=O)Oc2cc(C)cc(OCCCONC(=N)N)c2)cc1.Cl
3-[5-methyl-3-(2-(N-methyl-N-(4-methoxycarbonylphenyl)aminosulfonyl)phenylsulfonyloxy)phenoxy]propoxyguanidine hydrochloride

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeas prepared in step b of Example 50, in a manner analogous to Example 27

Vorschrift

The title compound was prepared in 84% yield from 3-[5-methyl-3-(2-(N-methyl-N-(4-methoxycarbonylphenyl)aminosulfonyl)phenylsulfonyloxy)phenoxy]propoxyguanidine hydrochloride, as prepared in step b of Example 50, in a manner analogous to Example 27. 1H-NMR (300 MHz, DMSO-d6) δ 8.17 (d, J=7.4 Hz, 1H), 7.97 (t, J=7.6 Hz, 1H), 7.90 (m, 4H), 7.61 (br s, 4H), 7.40 (d, J=7.7 Hz, 2H), 6.74 (s, 1H), 6.45 (s, 2H), 3.98 (t, J=6.2 Hz, 2H), 3.90 (t, J=6.3 Hz, 2H), 3.46 (s, 3H), 2.19 (s, 3H), 2.01 (pentet, J=6.2 Hz, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C25H28N4O9S2: 593.1 (M+H), 615.1 (M+Na), 631.1 (M+K). Found: 593.1, 615.0, 630.9.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06706765B2uspto-grants-2004_03