Dichloromethane → HCID 178504998, compound

HRID 1792528Notes

Reaction equation

HRID 1792528 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:24][CH:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.ClCCl.[OH-].[Na+]>O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])=[CH:24][CH:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 22031841HCID 22031841, compound

Product 1

HCID 178504998HCID 178504998, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 71 mg N-(4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenyl)-methane sulfonamide obtained in Example 20, 0.36 mL trifluoroacetic acid and 5 mL dichloromethane was stirred overnight at room temperature. The reaction solution was cooled and made weakly alkaline with 5 N aqueous sodium hydroxide, followed by adding ethyl acetate and water to separate an organic layer. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, the filtrate was evaporated, the residue was triturated with diethyl ether, and the crystals were separated by filtration. This product was dried under vacuum to give 33 mg of the title compound as a white solid.

Workup

  1. temperatureThe reaction solution was cooled
  2. customto separate an organic layer
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe filtrate was evaporated
  7. customthe residue was triturated with diethyl ether
  8. customthe crystals were separated by filtration
  9. customThis product was dried under vacuum

Sources & evidence

ORD record
ord-3f3a3ddd8e994a8ea7894fc41e311a1d
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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