Sodium hydride → HCID 66939685, compound

HRID 1257431Notes

Reaction equation

HRID 1257431 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[N:4]1.Cl[CH2:14][C:15]1[S:19][C:18]([CH3:20])=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[CH:16]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:20][C:18]1[S:19][C:15]([CH2:14][N:3]2[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[N:4]2)=[CH:16][C:17]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 66939592HCID 66939592, compound

Product 1

HCID 66939685HCID 66939685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of sodium hydride (55% in mineral oil, 0.11 g) in tetrahydrofuran (4 mL) was cooled in an ice bath, and a solution of ethyl 1H-pyrazole-4-carboxylate (0.29 g) in tetrahydrofuran (2 mL) was added dropwise. The mixture was stirred at room temperature for 30 min, and a solution of the compound obtained in Example 126d in tetrahydrofuran (2 mL) was added dropwise. After stirring at room temperature for 6 hr, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (0.20 g) as a solid.

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringAfter stirring at room temperature for 6 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4dd5fd25569d407e9588a076cebbb738
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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