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

HRID 482096ノート

反応式

HRID 482096 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-c147a9594b76417794d23f7130dd9016
出典データセット
uspto-grants-1998_08
特許番号
US05792769

反応ノート

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