Hydrochloric Acid → HCID 86619009, compound

HRID 2388631Notes

Reaction equation

HRID 2388631 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[CH:8]=[C:9]([NH:24][C:25]([C:27]2[C:32]([CH3:33])=[N:31][CH:30]=[CH:29][N:28]=2)=[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].[CH2:34]([O:36][CH2:37]Cl)[CH3:35].Cl>C1COCC1>[CH2:34]([O:36][CH2:37][N:24]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:22][CH3:23])([C:18]([F:20])([F:21])[F:19])[C:14]([F:17])([F:16])[F:15])=[C:7]([CH2:3][CH:4]([CH3:6])[CH3:5])[CH:8]=1)[C:25]([C:27]1[C:32]([CH3:33])=[N:31][CH:30]=[CH:29][N:28]=1)=[O:26])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 86619008HCID 86619008, compound

Product 1

HCID 86619009HCID 86619009, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Sodium hydride (32 mg, 60% by weight, 0.8 mmol) was suspended in THF (10 ml) and a THF (5 ml) solution of N-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-3-methylpyrazine-2-carboxamide (300 mg, 0.67 mmol) was added dropwise thereto. The reaction solution was stirred at room temperature for 30 minutes, and was added with a THF (2 ml) solution of chloromethyl ethyl ether (76 mg, 0.8 mmol) and stirred for 5 hours. The reaction solution was poured into a diluted HCl solution, followed by extracting with ethyl acetate, and washing with water. The solution was dried over magnesium sulfate, and concentrated under reduced pressure, and then the residue was purified by using silica gel chromatography (hexane:ethyl acetate=3:1) to obtain 0.24 g of the desired compound.

Workup

  1. stirringstirred for 5 hours
  2. extractionby extracting with ethyl acetate
  3. washwashing with water
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified

Sources & evidence

ORD record
ord-359da5fbb3e84bb3b65285cca82aff9e
Source dataset
uspto-grants-2012_09
Patent number
US08269045B2

Reaction notes

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