Triphenylphosphine → 4-Chloro-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinoline

HRID 393642

反応式

HRID 393642 の反応式
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:26])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][CH:15]=1.[N:27]1([CH2:32][CH2:33]O)[CH:31]=[N:30][CH:29]=[N:28]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH2:33][CH2:32][N:27]3[CH:31]=[N:30][CH:29]=[N:28]3)=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5509251H-1,2,4-Triazole-1-ethanolHCID 1355837314-Chloro-6-methoxyquinolin-7-ol

生成物 1

HCID 226465544-Chloro-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinoline収率 45%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Diethyl azodicarboxylate (1 ml, 6.5 mmol) was added dropwise to a solution of 4-chloro-7-hydroxy-6-methoxyquinoline (845 mg, 4.0 mmol), (prepared as described for the starting material in Example 3), 2-([1,2,4]-triazol-1-yl)ethanol (500 mg, 4.4 mmol), (Ann. Pharm. Fr. 1977, 35, 503-508), and triphenylphosphine (1.7 g, 6.5 mmol) in methylene chloride (40 ml) under argon. After stirring for 4 days at ambient temperature, the insoluble materials were removed by filtration. The volatiles were removed by evaporation and the residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (75/20/5). The product was purified by a second chromatography on neutral alumina eluting with methylene chloride/acetonitrile/methanol (75/20/5). The purified product was triturated with ether, collected by filtration and dried under vacuum to give 4-chloro-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinoline (544 mg, 45%).

後処理

  1. custom(prepared
  2. customthe insoluble materials were removed by filtration
  3. customThe volatiles were removed by evaporation
  4. customthe residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (75/20/5)
  5. customThe product was purified by a second chromatography on neutral alumina eluting with methylene chloride/acetonitrile/methanol (75/20/5)
  6. customThe purified product was triturated with ether
  7. filtrationcollected by filtration
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-8d3f5f227766422fabf12c317ca2b63e
出典データセット
uspto-grants-2004_10
特許番号
US06809097B1

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