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6-Fluoro4-(3-hydroxy-4-methyl-phenylamino)-[1,7]naphthyridine-3-carbonitrile → 6-(2-Dimethylamino-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-[1,7]naphthyridine-3-carbonitrile

HRID 276872
ノート
印刷プレビュー

反応式

HRID 276872 の反応式
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([OH:22])[CH:16]=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][O-:27].[Na+]>O1CCCC1.O>[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][O:27][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([OH:22])[CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 185489376-Fluoro4-(3-hydroxy-4-methyl-phenylamino)-[1,7]naphthyridine-3-carbonitrileHCID 23680072Sodium (2dimethylamino-ethoxide)

生成物 1

HCID 185489466-(2-Dimethylamino-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-[1,7]naphthyridine-3-carbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To 160 mg of 6-fluoro-4-(3-hydroxy-4-methyl-phenylamino)-[1.7]naphthyridine-3-carbonitrile under an inert atmosphere was added 3 mL of 1 M sodium (2-dimethylamino-ethoxide) in tetrahydrofuran. After refluxing for 3 hours, the reaction was diluted with water and the product extracted five times with chloroform. The crude product was purified by flash chromatography with 1% triethyl amine and 10% methanol/chloroform followed by recrystallized from chloroform/ether to give 106 mg of 6-(2-dimethylamino-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-[1.7]naphthyridine-3-carbonitrile as a yellowish solid: melting point 100-180° C. (decomposed, effervescence); mass spectrum (m/e): M+H 419.9.

後処理

  1. temperatureAfter refluxing for 3 hours
  2. extractionthe product extracted five times with chloroform
  3. customThe crude product was purified by flash chromatography with 1% triethyl amine and 10% methanol/chloroform
  4. customby recrystallized from chloroform/ether

出典と根拠

ORDレコード
ord-46131189663c43019d2bd61871b560a2
出典データセット
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06355636B1

反応ノート

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