Triphenylphosphine → 4-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline-3-carbonitrile

HRID 347324

反応式

HRID 347324 の反応式
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([OH:28])=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[CH:18][C:17]=1[C:29]#[N:30].O[CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.O>[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[CH:18][C:17]=1[C:29]#[N:30]

参加物

7

反応物 4

HCID 11776Triphenylphosphine2 回HCID 75555Diisopropyl diazene-1,2-dicarboxylate2 回HCID 792083-(4-Methyl-1-piperazine)propan-1-olHCID 1357436694-Chloro-7-hydroxy-6-methoxyquinoline-3-carbonitrile

生成物 1

HCID 117491774-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline-3-carbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
5 °C

実験手順

A solution of diisopropyl azodicarboxylate (12.1 ml) in methylene chloride (50 ml) was added dropwise during 30 minutes to a stirred mixture of 4-chloro-3-cyano-7-hydroxy-6-methoxyquinoline (12 g), 1-(3-hydroxypropyl)-4-methylpiperazine (9.7 g), triphenylphosphine (16.1 g) and methylene chloride (200 ml) that had been cooled to 5° C. The resultant mixture was allowed to warm to ambient temperature and was then stirred for 1 hour. Further portions of diisopropyl azodicarboxylate (1.2 ml) and triphenylphosphine (1.6 g) were added and the mixture was stirred at ambient temperature for a further 1 hour. The mixture was poured into water and the organic layer was separated, washed with a saturated brine solution, dried over magnesium sulphate and evaporated. The material so obtained was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained the required starting material as a solid (14.5 g); NMR Spectrum: (DMSOd6) 1.95 (m, 2H), 2.13 (s, 3H), 2.24–2.5 (m, 10H), 4.0 (s, 3H), 4.25 (t, 2H), 7.43 (s, 1H), 7.51 (s, 1H), 8.95 (s, 1H); Mass Spectrum: M+H+ 375 and 377.

後処理

  1. temperatureto warm to ambient temperature
  2. stirringthe mixture was stirred at ambient temperature for a further 1 hour
  3. customthe organic layer was separated
  4. washwashed with a saturated brine solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe material so obtained
  8. customwas purified by column chromatography on silica using
  9. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  10. customThere was thus obtained the

出典と根拠

ORDレコード
ord-fccd35cb9d694bdd895561c7bbd803c6
出典データセット
uspto-grants-2007_02
特許番号
US07173136B2

関連ノート

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