Potassium Carbonate → HCID 68496027、化合物

HRID 388498ノート

反応式

HRID 388498 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]([C:17]1([C:20](=[O:46])[NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][N:32]=[C:31]([NH:35][C:36](OC4C=CC=CC=4)=[O:37])[CH:30]=3)=[CH:24][C:23]=2[F:45])[CH2:19][CH2:18]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:47][N:48]1[CH2:53][CH2:52][N:51]([CH:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)[CH2:50][CH2:49]1>CN(C)C=O>[CH2:7]([O:14][C:15]([C:17]1([C:20](=[O:46])[NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH:29]3[CH2:34][CH2:33][NH:32][CH:31]([NH:35][C:36]([N:57]4[CH2:58][CH2:59][CH:54]([N:51]5[CH2:52][CH2:53][N:48]([CH3:47])[CH2:49][CH2:50]5)[CH2:55][CH2:56]4)=[O:37])[CH2:30]3)=[CH:24][C:23]=2[F:45])[CH2:18][CH2:19]1)=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 247886951-[2-Fluoro-4-(2-phenoxycarbonylaminopyridin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester

生成物 1

HCID 68496027HCID 68496027、化合物収率 49.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Potassium carbonate (772 mg) was added to a mixture of 1-[2-fluoro-4-(2-phenoxycarbonylaminopyridin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester (2.75 g) and N,N-dimethylformamide (13.8 ml) was added, followed by stirring. 1-Methyl-4-(piperidin-4-yl)piperazine (1.02 g) was added, followed by stirring for 6 hours. The reaction mixture was partitioned after the addition of ethyl acetate (41 ml) and water (27.5 ml). The resultant organic layer was washed with water (13.8 ml, three times), dried over sodium sulfate, and filtered, and the filtrate was concentrated. The resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:methanol=30:1). The eluate was concentrated under reduced pressure, and the precipitate appeared by the addition of tert-butyl methyl ether (3 ml) and the application of a stimulus. tert-Butyl methyl ether (40 ml) was further added, followed by stirring overnight. The resultant precipitate was collected by filtration, washed with tert-butyl methyl ether (3 ml), and dried under aeration to give the target title compound (1.61 g).

後処理

  1. additionwas added
  2. stirringby stirring for 6 hours
  3. customThe reaction mixture was partitioned
  4. additionafter the addition of ethyl acetate (41 ml) and water (27.5 ml)
  5. washThe resultant organic layer was washed with water (13.8 ml, three times)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:methanol=30:1)
  10. concentrationThe eluate was concentrated under reduced pressure
  11. additionthe precipitate appeared by the addition of tert-butyl methyl ether (3 ml)
  12. additiontert-Butyl methyl ether (40 ml) was further added
  13. stirringby stirring overnight
  14. filtrationThe resultant precipitate was collected by filtration
  15. washwashed with tert-butyl methyl ether (3 ml)
  16. customdried under aeration

出典と根拠

ORDレコード
ord-3d35c5565715492e89b42b6366cd929e
出典データセット
uspto-grants-2013_02
特許番号
US08377938B2

反応ノート

読み込み中…