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N-(2,2-dimethoxyethyl)-2-Pyrazinamine → 2-{2-[7-Chloro-6-[3-(2,2-dimethoxyethyl)-3-pyrazin-2-yl-ureido]-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester

HRID 1858080
ノート
印刷プレビュー

反応式

HRID 1858080 の反応式
[CH3:1][O:2][CH:3]([O:12][CH3:13])[CH2:4][NH:5][C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1.C([Li])CCC.[CH3:19][Si:20]([CH3:59])([CH3:58])[CH2:21][CH2:22][O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[CH2:32][CH2:33][O:34][C:35]1[C:44]2[C:39](=[CH:40][C:41]([Cl:48])=[C:42]([N:45]=[C:46]=[O:47])[CH:43]=2)[NH:38][C:37](=[O:49])[C:36]=1[C:50]1[CH:55]=[C:54]([CH3:56])[CH:53]=[C:52]([CH3:57])[CH:51]=1)=[O:25]>>[CH3:58][Si:20]([CH3:19])([CH3:59])[CH2:21][CH2:22][O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[CH2:32][CH2:33][O:34][C:35]1[C:44]2[C:39](=[CH:40][C:41]([Cl:48])=[C:42]([NH:45][C:46]([N:5]([CH2:4][CH:3]([O:2][CH3:1])[O:12][CH3:13])[C:6]3[CH:11]=[N:10][CH:9]=[CH:8][N:7]=3)=[O:47])[CH:43]=2)[NH:38][C:37](=[O:49])[C:36]=1[C:50]1[CH:55]=[C:54]([CH3:56])[CH:53]=[C:52]([CH3:57])[CH:51]=1)=[O:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 3

HCID 22124488N-(2,2-dimethoxyethyl)-2-PyrazinamineHCID 539605652-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-isocyanato-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl esterHCID 178418339Butyllithium

生成物 1

HCID 544133062-{2-[7-Chloro-6-[3-(2,2-dimethoxyethyl)-3-pyrazin-2-yl-ureido]-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester
収率 9%

実験手順

To a solution of (2,2-dimethoxyethyl)-pyrazin-2-yl-amine (103 mg in 3 mL dry tetrahydrofuran) at -78° C. was added 0.23 mL of a 2.5M solution of butyllithium and the mixture stirred for 30 minutes. At this time, a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-isocyanato-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester (94 mg in 2 mL tetrahydrofuran) was added via cannula and the mixture warmed to room temperature. After 20 hours, the reaction was quenched by the addition of saturated ammonium chloride and extracted with chloroform. The organic portion was washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification of the residue by preparative tlc on silica gel (ethyl acetate) gave the title compound (11 mg).

後処理

  1. waitAfter 20 hours
  2. customthe reaction was quenched by the addition of saturated ammonium chloride
  3. extractionextracted with chloroform
  4. washThe organic portion was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by preparative tlc on silica gel (ethyl acetate)

出典と根拠

ORDレコード
ord-7da0a3eb687b4a18950504c3d7322933
出典データセット
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06150352

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート