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

HRID 482096노트

반응식

HRID 482096 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c147a9594b76417794d23f7130dd9016
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792769

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