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Ethyl orthoformate → 4-(4-Cyano-2-methoxyphenyl)-5-ethoxy-2,7-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carbonitrile

HRID 1951424
ノート
印刷プレビュー

反応式

HRID 1951424 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[NH:16][C:15]([CH3:20])=[CH:14][C:13]=3[NH:12][C:11]([CH3:21])=[C:10]2[C:22]#[N:23])=[C:5]([O:24][CH3:25])[CH:4]=1)#[N:2].C(OCC)(OCC)O[CH2:28][CH3:29]>S(=O)(=O)(O)O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([CH3:20])=[N:16][C:17]=3[O:19][CH2:28][CH3:29])[NH:12][C:11]([CH3:21])=[C:10]2[C:22]#[N:23])=[C:5]([O:24][CH3:25])[CH:4]=1)#[N:2]
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 2

HCID 31214Ethyl orthoformateHCID 674174494-(4-Cyano-2-methoxyphenyl)-2,7-dimethyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carbonitrile

生成物 1

HCID 674183464-(4-Cyano-2-methoxyphenyl)-5-ethoxy-2,7-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carbonitrile

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

反応条件

温度
130 °C

実験手順

1920 mg (5.77 mmol) of 4-(4-cyano-2-methoxyphenyl)-2,7-dimethyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carbonitrile are suspended in 40 ml (240 mmol) of anhydrous triethyl orthoformate. The reaction mixture is heated to 130° C. Then 10 drops of concentrated sulfuric acid are added each hour. After complete reaction has been detected (analytical HPLC; reaction time about 36 h), the reaction mixture is cooled to room temperature, and the volatile components are removed in a rotary evaporator. The crude product is purified by column chromatography (silica gel; mobile phase: cyclohexane/ethyl acetate 1:1). The product obtained in this way is crystallized from ethyl acetate. 451 mg (22% of theory) of the title compound are obtained as a white solid.

後処理

  1. customAfter complete reaction
  2. custom(analytical HPLC; reaction time about 36 h)
  3. temperaturethe reaction mixture is cooled to room temperature
  4. customthe volatile components are removed in a rotary evaporator
  5. customThe crude product is purified by column chromatography (silica gel; mobile phase: cyclohexane/ethyl acetate 1:1)
  6. customThe product obtained in this way
  7. customis crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-c20a093fa2fe43bcb7979604b7c3124c
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08404709B2

反応ノート

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