Triethylamine → 2-Chlorobenzenesulfonic acid 3-[[1-(aminoiminomethyl)piperidin-4-yl]methoxy]phenyl ester

HRID 482083ノート

反応式

HRID 482083 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([O:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[NH2:33][N:34]=[CH:35]S(O)(=O)=O>CN(C=O)C>[NH2:33][N:34]=[CH:35][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([O:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])(=[O:17])=[O:18])[CH:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 3013981Aminoiminomethane-sulphonic acidHCID 542506032-Chlorobenzenesulfonic acid 3-[(piperidin-4-yl)methoxy]phenyl ester

生成物 1

HCID 867530142-Chlorobenzenesulfonic acid 3-[[1-(aminoiminomethyl)piperidin-4-yl]methoxy]phenyl ester収率 49.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2-chlorobenzenesulfonic acid 3-[(piperidin-4-yl)methoxy]phenyl ester (191 mg, 0.5 mmol), as prepared in the preceding step, in DMF (10 mL) containing triethylamine (0.2 mL) and aminoiminomethanesulfonic acid (124 mg, 1.0 mmol) was stirred at room temperature overnight. The DMF was concentrated in vacuo and the residue was purified by flash column chromatography (90: 10 methylene chloride:methanol saturated with NH3) to give the title compound as a white foam (105 mg, 49%). 1H-NMR (300 MHz, CDCl3 /DMSO)-d6) δ 1.38 (m, 2H), 1.88 (d, 2H), 2.08 (m, 1H), 3.00 (t, 2H), 3.79 (d, 2H), 4.05 (dd, 2H), 6.61 (dd, 1H) 6.77 (t, 1H), 6.79 (dd, 1H), 7.20 (t, 1H), 7.37 (bs, 3H), 7.50 (m, 1H), 7.92 (d, 2H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C19H22 N3O4SCl: 424.1(M+H), 446.1 (M+Na), Found: 424.3, 446.6

後処理

  1. concentrationThe DMF was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography (90: 10 methylene chloride:methanol saturated with NH3)

出典と根拠

ORDレコード
ord-1a53372764f94659aafa9ca611313385
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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