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

HRID 1712665노트

반응식

HRID 1712665 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-24c17dab890b44b9a897954d01e1d40e
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790885B2

반응 노트

불러오는 중…