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

HRID 482094Notes

Reaction equation

HRID 482094 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: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

Participants

5

Reactant 3

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

Product 1

HCID 867530172-Chlorobenzenesulfonic acid 3-[2-[1-(aminoiminomethyl)piperazin-4-yl]ethoxy]phenyl ester diacetic acid saltYield 155.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-78749b264eae43c4941a163f73c2f64b
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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