Water → HCID 58806675, compound

HRID 351269Notes

Reaction equation

HRID 351269 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]([C:19]3[CH:20]=[N:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[N:17]=[C:16]([CH:27]([F:29])[F:28])[CH:15]=2)=[CH:10][CH:9]=1)(=O)=O.[OH2:30].[CH3:31][N:32]([CH:34]=[O:35])C>>[F:29][CH:27]([F:28])[C:16]1[CH:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][N:32]3[C:31](=[O:30])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:34]3=[O:35])=[CH:9][CH:10]=2)[N:18]([C:19]2[CH:20]=[N:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[N:17]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 21090800HCID 21090800, compound

Product 1

HCID 58806675HCID 58806675, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 2-{4-[3-(difluoromethyl)-1-(6-methoxy-3-pyridinyl)-1H-pyrazol-5-yl]phenyl}ethyl methanesulfonate (7.4 g) and Ph(CO) 2NK (3.88 g) in DMF (50 ml) was stirred at 60° C. for 8 hours. Added water. The organic layer was extracted twice with EtOAc. Aqueous layer was washed with water (twice) and brine, dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was triturated with IPE, filtered and dried to give 7.65 g of 2-(2-{4-[3-(difluoromethyl)-1-(6-methoxy-3-pyridinyl)-1H-pyrazol-5-yl]phenyl}ethyl)-1H-isoindole-1,3 (2H)-dione as a solid.

Workup

  1. extractionThe organic layer was extracted twice with EtOAc
  2. washAqueous layer was washed with water (twice) and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with IPE
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-466a6bbad6b1497bad6606d7c419c81e
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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