Acetonitrile → 1-[2-Fluoro-4-(2-phenoxycarbonylaminopyridin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester

HRID 1712665ノート

反応式

HRID 1712665 の反応式
O1CCCC1.C(#N)C.[CH2:9]([O:16][C:17]([C:19]1([C:22](=[O:39])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][N:34]=[C:33]([NH2:37])[CH:32]=3)=[CH:26][C:25]=2[F:38])[CH2:21][CH2:20]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[C:41]([O:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:42]>N1C=CC=CC=1>[CH2:9]([O:16][C:17]([C:19]1([C:22](=[O:39])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][N:34]=[C:33]([NH:37][C:41]([O:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:42])[CH:32]=3)=[CH:26][C:25]=2[F:38])[CH2:20][CH2:21]1)=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 15891Phenyl chloroformateHCID 594597071-[4-(2-Aminopyridin-4-yloxy)-2-fluorophenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester

生成物 1

HCID 247886951-[2-Fluoro-4-(2-phenoxycarbonylaminopyridin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester収率 82.9%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Tetrahydrofuran (41 ml), acetonitrile (41 ml) and pyridine (2.07 g) was added to 1-[4-(2-aminopyridin-4-yloxy)-2-fluorophenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester (6.0 g, content 5.51 g), which was dissolved by stirring. Phenyl chloroformate (4.1 g) was added dropwise to this solution with cooling on ice at the internal temperature between 8.8° C. and 14.9° C. The reaction mixture was stirred at the same temperature for 2 hours and 9 minutes, then at room temperature for 3 hours and 5 minutes. The precipitate was collected by filtration, washed with a mixed solvent of tetrahydrofuran and acetonitrile (2:1, 16 ml), and dried under aeration to give the target title compound (6.39 g).

後処理

  1. dissolutionwas dissolved
  2. temperaturewith cooling on ice at the internal temperature between 8.8° C. and 14.9° C
  3. stirringThe reaction mixture was stirred at the same temperature for 2 hours and 9 minutes
  4. custom5 minutes
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with a mixed solvent of tetrahydrofuran and acetonitrile (2:1, 16 ml)
  7. customdried under aeration

出典と根拠

ORDレコード
ord-24c17dab890b44b9a897954d01e1d40e
出典データセット
uspto-grants-2010_09
特許番号
US07790885B2

反応ノート

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