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Water → ethyl 3-[3-phenyl-1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate

HRID 350291
Notes
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Reaction equation

HRID 350291 reaction equation
[H-].[Na+].Cl[CH2:4][C:5]1[CH:23]=[CH:22][C:8]([O:9][CH2:10][C:11]2[N:12]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:14][CH:15]=2)=[CH:7][CH:6]=1.[C:24]1([C:30]2[C:34]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:33][NH:32][N:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C)C=O>[C:24]1([C:30]2[C:34]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:33][N:32]([CH2:4][C:5]3[CH:23]=[CH:22][C:8]([O:9][CH2:10][C:11]4[N:12]=[C:13]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)[S:14][CH:15]=4)=[CH:7][CH:6]=3)[N:31]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 178613834-(4-Chloromethylphenoxy)methyl-2-phenylthiazoleHCID 178471160HCID 178471160, compound

Product 1

HCID 23024833ethyl 3-[3-phenyl-1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionateYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 110 mg) was added to a solution of 4-(4-chloromethylphenoxymethyl)-2-phenylthiazole (760 mg) and ethyl 3-(3-phenyl-1H-pyrazol-4-yl)propionate (580 mg) in N,N-dimethylformamide (10 ml) at 0° C., and the mixture was stirred at room temperature for 2 hours. 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-phenyl-1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate (1110 mg, yield: 89%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:2, 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-cda01829a72e4d3b9e2bf4c62109483e
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179823B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes