Hydrochloric Acid → 3-Cyano-7-ethoxy-6-methoxy-4-[4-(3-methoxyprop-1-ynyl)-2,3-methylenedioxyanilino]quinoline monohydrochloride salt

HRID 347426

反応式

HRID 347426 の反応式
C[Si](C)(C)N[Si](C)(C)C.[Na].[CH3:11][O:12][CH2:13][C:14]#[C:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]2[O:23][CH2:24][O:25][C:17]=12.[Cl:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([O:39][CH2:40][CH3:41])=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][C:28]=1[C:42]#[N:43].Cl>O.C(Cl)Cl.C(OCC)C.CN(C=O)C>[ClH:26].[C:42]([C:28]1[CH:29]=[N:30][C:31]2[C:36]([C:27]=1[NH:20][C:19]1[CH:21]=[CH:22][C:16]([C:15]#[C:14][CH2:13][O:12][CH3:11])=[C:17]3[O:25][CH2:24][O:23][C:18]=13)=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH2:40][CH3:41])[CH:32]=2)#[N:43]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 105634734-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrileHCID 210827034-(3-Methoxyprop-1-ynyl)-2,3-methylendioxyanilineHCID 45051731Sodium hexamethyidisilazane

生成物 1

HCID 210826963-Cyano-7-ethoxy-6-methoxy-4-[4-(3-methoxyprop-1-ynyl)-2,3-methylenedioxyanilino]quinoline monohydrochloride salt収率 69.2%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Sodium hexamethyldisilazane (1M solution in THF; 1.17 ml) was added to a stirred mixture of 4-(3-methoxyprop-1-ynyl)-2,3-methylenedioxyaniline (0.12 g), 4-chloro-3-cyano-7-ethoxy-6-methoxyquinoline (0.146 g) and DMF (8 ml) that had been cooled to 0° C. and the resultant mixture was allowed to warm to ambient temperature and was stirred for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and with a saturated brine solution, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica increasingly polar mixtures of methylene chloride and methanol as eluent. The material so obtained was dissolved in the minimum quantity of methylene chloride. The solution was diluted with diethyl ether and a solution of hydrogen chloride in diethyl ether (1M) was added. The resultant solid was isolated, washed with diethyl ether and dried. Thereby, the product was obtained the title compound (0.18 g); NMR Spectrum: (DMSOd6) 1.44 (t, 3H), 3.33 (s, 3H), 4.0 (s, 3H), 4.24 (q, 2H), 4.36 (s, 2H), 6.12 (s, 2H), 6.96 (d, 1H), 7.03 (d, 1H), 7.45 (s, 1H), 8.11 (s, 1H), 8.96 (s, 1H); Mass Spectrum: M+H+ 432.

後処理

  1. temperatureto warm to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and with a saturated brine solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica
  7. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  8. customThe material so obtained
  9. customThe resultant solid was isolated
  10. washwashed with diethyl ether
  11. customdried

出典と根拠

ORDレコード
ord-bccc0d496dfa48beb370028bd827b56f
出典データセット
uspto-grants-2007_02
特許番号
US07173135B2

関連ノート

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