Diisopropylethylamine → 3-(4-{[6-({2-Hydroxy-2-[5-hydroxy-6-(hydroxymethyl)pyridin-2-yl]ethyl}amino)hexyl]oxy}butyl)benzenesulfonamide formate

HRID 749253

反応式

HRID 749253 の反応式
[NH2:1][CH2:2][CH:3]([C:5]1[N:10]=[C:9]2[CH2:11][O:12][CH:13](C3C=CC=CC=3)[O:14][C:8]2=[CH:7][CH:6]=1)[OH:4].C(N(C(C)C)CC)(C)C.Br[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]1[CH:43]=[C:44]([S:48]([NH2:51])(=[O:50])=[O:49])[CH:45]=[CH:46][CH:47]=1>CN(C)C=O>[CH:13]([OH:14])=[O:12].[OH:4][CH:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:14])=[C:9]([CH2:11][OH:12])[N:10]=1)[CH2:2][NH:1][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]1[CH:43]=[C:44]([S:48]([NH2:51])(=[O:50])=[O:49])[CH:45]=[CH:46][CH:47]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 21895438Benzenesulfonamide, 3-[4-[(6-bromohexyl)oxy]butyl]-HCID 688660332-amino-1-(2-phenyl-4H-[1,3]dioxino[5,4-b]pyridin-6-yl)ethanol

生成物 1

HCID 693214693-(4-{[6-({2-Hydroxy-2-[5-hydroxy-6-(hydroxymethyl)pyridin-2-yl]ethyl}amino)hexyl]oxy}butyl)benzenesulfonamide formate収率 22.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A stirred solution of 2-amino-1-(2-phenyl-4H-[1,3]dioxino[5,4-b]pyridin-6-yl)ethanol (100 mg) (EP220054A2), diisopropylethylamine (0.08 ml) and 3-{4-[(6-bromohexyl)oxy]butyl}benzenesulfonamide (120 mg) in N,N-dimethylformamide (2 ml) under nitrogen was heated to 50° for 18 h. The mixture was cooled to 20° and the solvent evaporated in vacuo. The residue was dissolved in acetic acid (4 ml) and water (2 ml) and was heated to 70° for 18 h. The mixture was cooled to 20°, the solvent evaporated in vacuo and the residue purified by mass-directed autopreparative HPLC to give the title compound (22 mg). LCMS RT=2.23 min, ES+ve 496 (MH)+.

後処理

  1. temperatureThe mixture was cooled to 20°
  2. customthe solvent evaporated in vacuo
  3. dissolutionThe residue was dissolved in acetic acid (4 ml)
  4. temperaturewater (2 ml) and was heated to 70° for 18 h
  5. temperatureThe mixture was cooled to 20°
  6. customthe solvent evaporated in vacuo
  7. customthe residue purified by mass-directed autopreparative HPLC

出典と根拠

ORDレコード
ord-d11b74b3a7094aacb354d613d9c0fa96
出典データセット
uspto-grants-2008_07
特許番号
US07402598B2

関連ノート

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