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methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate → 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acid

HRID 1399791
ノート
印刷プレビュー

反応式

HRID 1399791 の反応式
[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:12][C:13]([C:14]([O:16]C)=[O:15])=[C:8]2[N:7]=[C:6]1[CH3:24]>[Li+].[OH-].C1COCC1>[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[C:8]2[N:7]=[C:6]1[CH3:24]
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

4

反応物 1

HCID 89648260methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

生成物 1

HCID 716106943-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acid収率 63%

試薬・触媒・溶媒 2

HCID 3939Lithium Hydroxide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A mixture of methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate (239 mg, 0.55 mmol) in 2N LiOH (15 mL) and THF (15 mL) was stirred at 60° C. for 5 h. It was cooled to room temperature and the precipitate was collected by filtration. It was then poured into water (50 mL) and the suspension was acidified with formic acid to pH=1. It was filtered and the solid was washed with water to afford the desired product as a gray solid (146 mg, 63%); LC/MS: MS (ES+) m/e 421 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.46 (s, 3H), 3.39 (t, J=4.8 Hz, 4H), 3.67 (t, J=4.8 Hz, 4H), 5.50 (s, 2H), 6.67 (d, J=4.5 Hz, 1H), 7.04 (s, 1H), 7.28 (t, J=7.5 Hz, 1H), 7.60 (d, J=4.5 Hz, 1H), 8.14 (s, 1H).

後処理

  1. temperatureIt was cooled to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. additionIt was then poured into water (50 mL)
  4. filtrationIt was filtered
  5. washthe solid was washed with water

出典と根拠

ORDレコード
ord-4461bd9a640f485b870c29e1cba5f220
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08906910B2

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