Water → HCID 23024737, compound

HRID 350239Notes

Reaction equation

HRID 350239 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[C:10]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][NH:8][N:7]=1)[CH3:4].ClCC1ON=C([CH2:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)C=1.[OH2:36]>CN(C)C=O>[CH2:3]([O:5][C:6]1[C:10]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][N:8]([CH2:12][C:11]2[O:36][N:7]=[C:6]([O:5][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=3)[CH:10]=2)[N:7]=1)[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 23024963HCID 23024963, compoundHCID 178471163HCID 178471163, compound

Product 1

HCID 23024737HCID 23024737, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 70.0 mg) was added to a solution of ethyl 3-(3-ethoxy-1H-pyrazol-4-yl)propionate (371 mg) and 2-(5-chloromethyl-3-isoxazolylmethyl)quinoline (481 mg) in N,N-dimethylformamide (10 ml) at 0° C., and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain-ethyl 3-[3-ethoxy-1-[3-(2-quinolylmethoxy)-5-isoxazolylmethyl]-1H-pyrazol-4-yl]propionate (722 mg, yield: 92%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-77c6504b819e4f7a842283f88db68c0c
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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