Hydrochloric Acid → HCID 86619007, compound

HRID 2388630Notes

Reaction equation

HRID 2388630 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].[C:34](Cl)(=[O:40])[O:35][CH2:36][CH:37]([CH3:39])[CH3:38].Cl>C1COCC1>[CH2:36]([O:35][C:34]([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])=[O:40])[CH:37]([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 62365Isobutyl chloroformateHCID 86619008HCID 86619008, compound

Product 1

HCID 86619007HCID 86619007, compoundYield 90%

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 solution (5 ml) 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 dropwise added thereto. The reaction solution was stirred at room temperature for 30 minutes, and was dropwise added with a THF (2 ml) solution of isobutyl chlorocarbonate (110 mg, 0.8 mmol) and stirred for 2 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 0.33 g of the desired compound.

Workup

  1. stirringstirred for 2 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-3813f6c7fd2047dca9b5fc8cc4282800
Source dataset
uspto-grants-2012_09
Patent number
US08269045B2

Reaction notes

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