Hydrochloric Acid → HCID 86629853, compound

HRID 1952259Notes

Reaction equation

HRID 1952259 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[CH:8]=[C:9]([NH:24][C:25]([C:27]2[C:28]([C:34]([F:37])([F:36])[F:35])=[N:29][N:30]([CH3:33])[C:31]=2[CH3:32])=[O:26])[CH:10]=[CH:11][C:12]=1[C:13]([O:22][CH3:23])([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15])[CH:4]([CH3:6])[CH3:5].[CH3:38][O:39][CH2:40]Cl.Cl>O1CCCC1>[CH3:38][O:39][CH2:40][N:24]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:22][CH3:23])([C:18]([F:19])([F:20])[F:21])[C:14]([F:16])([F:15])[F:17])=[C:7]([CH2:3][CH:4]([CH3:6])[CH3:5])[CH:8]=1)[C:25]([C:27]1[C:28]([C:34]([F:37])([F:36])[F:35])=[N:29][N:30]([CH3:33])[C:31]=1[CH3:32])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 15950608HCID 15950608, compound

Product 1

HCID 86629853HCID 86629853, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in tetrahydrofuran (10 ml), and a solution of N-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,5-dimethyl-3-trifluoromethylpyrazole-4-carboxamide (250 mg, 0.48 mmol) in tetrahydrofuran (5 ml) was added dropwise. After stirring at room temperature for 30 min, a solution of chloromethyl methyl ether (64 mg, 0.8 mmol) in tetrahydrofuran (2 ml) was added and the mixture was stirred for 5 hr. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired compound (238 mg).

Workup

  1. stirringthe mixture was stirred for 5 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-be73b56f4f9f450f816d44d6de725f63
Source dataset
uspto-grants-2013_03
Patent number
US08404861B2

Reaction notes

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