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Diisopropylethylamine → N-(4-Chlorobenzyl)-2-{[(2-hydroxy-2-pyridin-3-ylethyl)(methyl)amino]methyl}-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23637
ノート
印刷プレビュー

反応式

HRID 23637 の反応式
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:28])[C:12]3[S:19][C:18]([CH2:20]Cl)=[C:17]([CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:31][NH:32][CH2:33][CH:34]([C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)[OH:35].C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:28])[C:12]3[S:19][C:18]([CH2:20][N:32]([CH2:33][CH:34]([OH:35])[C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)[CH3:31])=[C:17]([CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:29][CH:30]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 224987342-(Methylamino)-1-(pyridin-3-yl)ethan-1-olHCID 22574279N-(4-chlorobenzyl)-2-(chloromethyl)-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

生成物 1

HCID 22574290N-(4-Chlorobenzyl)-2-{[(2-hydroxy-2-pyridin-3-ylethyl)(methyl)amino]methyl}-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide収率 92.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 111 mg of N-(4-chlorobenzyl)-2-(chloromethyl)-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide, 54 mg of 2-(methylamino)-1-pyridin-3-ylethanol (Arch. Pharm. (1961), 294, 453), and 62 μL of diisopropylethylamine in 1.5 mL of DMF is heated at 50° C. for 18 h, then cooled and partitioned between EtOAc and water. The organic phase is washed with two additional portions of water and brine, dried (Na2SO4), and concentrated under reduced pressure. Flash chromatography of the residue on silica using 5% MeOH in CH2Cl2 affords 128 mg of the title compound as a white foam. Recrystallization of a sample from EtOAc provides white crystals.

後処理

  1. temperaturecooled
  2. custompartitioned between EtOAc and water
  3. washThe organic phase is washed with two additional portions of water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-99c30a3ecf6a42fbab6a51cfdc446904
出典データセット
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06852731B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート