Diisopropylethylamine → 2-Chlorobenzenesulfonic acid 3-[2-[1-(aminoiminomethyl)piperazin-4-yl]ethoxy]phenyl ester diacetic acid salt

HRID 482094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482094
[NH:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([O:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[NH2:36][N:37]=[CH:38]S(O)(=O)=[O:40]>CN(C=O)C>[C:12]([OH:16])(=[O:40])[CH3:13].[C:12]([OH:16])(=[O:40])[CH3:13].[NH2:36][N:37]=[CH:38][N:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([O:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 3013981Aminoiminomethane-sulphonic acidHCID 178803862-Chlorobenzenesulfonic acid 3-[(piperazin-4-yl)ethoxy]phenyl ester

Produkt 1

HCID 867530172-Chlorobenzenesulfonic acid 3-[2-[1-(aminoiminomethyl)piperazin-4-yl]ethoxy]phenyl ester diacetic acid saltAusbeute 155,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-chlorobenzenesulfonic acid 3-[(piperazin-4-yl)ethoxy]phenyl ester (397 mg, 1.0 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.5 mL) and aminoiminomethanesulfonic acid (248 mg, 2.0 mmol) in DMF (10 mL) was stirred at room temperature overnight. The DMF was removed in vacuo and residue was purified by flash column chromatography (85:15:2 methylene chloride:methanol:acetic acid) to give the title compound as a white solid (290 mg, 52%). 1H-NMR (300 MHz, CDCl3 /CD3OD) δ 2.01 (bs, 6H), 2.64 (t, 4H), 2.84 (t, 2H), 3.45 (t, 4H), 4.07 (t, 2H), 6.67 (dd, 1H), 6.77 (t, 1H), 6.83 (dd, 1H), 7.19 (t, 1H), 7.41 (dt, 1H), 7.65 (t, 2H), 7.95 (dd, 1H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C19H23 N4O4SCl: 439.1(M+H), 461.1 (M+Na). Found: 438.8, 460.8.

Aufarbeitung

  1. customThe DMF was removed in vacuo and residue
  2. customwas purified by flash column chromatography (85:15:2 methylene chloride:methanol:acetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-78749b264eae43c4941a163f73c2f64b
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792769

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