Diisopropylethylamine → 2-Chlorobenzenesulfonic acid 3-[2-[1-(aminoiminomethyl)piperazin-4-yl]ethoxy]-5-methylphenyl ester diacetic acid salt

HRID 482096Notes

Reaction equation

HRID 482096 reaction equation
[NH:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([O:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])(=[O:20])=[O:19])[CH:13]=[C:14]([CH3:16])[CH:15]=2)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[NH2:37][N:38]=[CH:39]S(O)(=O)=[O:41]>CN(C=O)C>[C:12]([OH:17])(=[O:41])[CH3:13].[C:12]([OH:17])(=[O:41])[CH3:13].[NH2:37][N:38]=[CH:39][N:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([O:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])(=[O:20])=[O:19])[CH:13]=[C:14]([CH3:16])[CH:15]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3013981Aminoiminomethane-sulphonic acidHCID 539792122-Chlorobenzenesulfonic acid 3-[2-(piperazin-4-yl)ethoxy]-5-methylphenyl ester

Product 1

HCID 867530192-Chlorobenzenesulfonic acid 3-[2-[1-(aminoiminomethyl)piperazin-4-yl]ethoxy]-5-methylphenyl ester diacetic acid saltYield 154.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chlorobenzenesulfonic acid 3-[2-(piperazin-4-yl)ethoxy]-5-methylphenyl ester (411 mg, 1.0 mmol), as prepared in the preceding step, in DMF (10 mL) containing N,N-diisopropylethylamine (0.5 mL) and aminoiminomethanesulfonic acid (248 mg, 2.0 mmol) was stirred at room temperature overnight. The DMF was removed in vacuo and the residue was purified by flash column chromatography (85:15:2 methylene chloride:methanol:acetic acid) to give the title compound as a white solid (295 mg, 51%). 1H-NMR (300 MHz, CDCl3) δ 1.95 (s, 6H), 2.23 (s, 3H), 2.61 (t, 4H), 2.78 (t, 2H), 3.48 (t, 4H), 3.99 (t, 2H), 6.52 (s, 2H), 6.59 (s, 1H), 7.39 (dt, 1H), 7.62 (m, 2H), 7.96 (dd, 1H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C20H25N4O4SCl: 453.1(M+H), 475.1 (M+Na). Found: 452.7, 474.9.

Workup

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

Sources & evidence

ORD record
ord-c147a9594b76417794d23f7130dd9016
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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