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

HRID 1712665Notes

Reaction equation

HRID 1712665 reaction equation
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

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 15891Phenyl chloroformateHCID 59459707HCID 59459707, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-24c17dab890b44b9a897954d01e1d40e
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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