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

HRID 482094ノート

反応式

HRID 482094 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: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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-78749b264eae43c4941a163f73c2f64b
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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