Sodium ethoxide → HCID 68438105, compound

HRID 1437292Notes

Reaction equation

HRID 1437292 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[C:29](S(C)(=O)=O)[CH:28]=[CH:27][N:26]=3)[N:22]([C:35]3[CH:36]=[N:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=3)[N:21]=2)=[O:19])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>O1CCCC1>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[C:29]([O:1][CH2:2][CH3:3])[CH:28]=[CH:27][N:26]=3)[N:22]([C:35]3[CH:36]=[N:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=3)[N:21]=2)=[O:19])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxide2×HCID 57940688HCID 57940688, compound

Product 1

HCID 68438105HCID 68438105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

In an argon atmosphere, sodium ethoxide (28.4 mg) was added to a solution of 4-[1-(6-methoxy-3-pyridyl)-5-(4-methylsulfonyl-2-pyridyl)pyrazole-3-carbonyl]piperazine-1-carboxylic acid tert-butyl ester (0.189 g) obtained in Example 48 in tetrahydrofuran (3.8 mL) at room temperature. The resultant mixture was stirred for 1 hour, and then stirred for 90 minutes at 80° C. Subsequently, sodium ethoxide (85.2 mg) was added thereto. The mixture was stirred at 80° C. for 2 hours and 20 minutes, and then cooled in air. The resultant mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate-chloroform), to thereby give 4-[5-(4-ethoxy-2-pyridyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carbonyl]piperazine-1-carboxylic acid tert-butyl ester (0.139 g, 79%) as a solid.

Workup

  1. stirringThe mixture was stirred at 80° C. for 2 hours and 20 minutes
  2. temperaturecooled in air
  3. customThe resultant mixture was partitioned between water and ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (ethyl acetate-chloroform)

Sources & evidence

ORD record
ord-38289fbdcd574bf4b23473b748ff198f
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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