Dimethylformamide → HCID 86605785, compound

HRID 2221816Notes

Reaction equation

HRID 2221816 reaction equation
Cl[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[O:12][C:13]=2[CH3:14])=[C:5]([O:22][CH3:23])[CH:4]=1.[OH:24][C:25]1[C:29]([CH2:30][CH:31]2[S:35][C:34](=[O:36])[NH:33][C:32]2=[O:37])=[CH:28][N:27]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:26]=1.[CH3:44]N(C)C=O.[H-].[Na+]>O>[O:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:11]1[O:12][C:13]([CH3:14])=[C:9]([CH2:8][O:7][C:6]2[CH:20]=[CH:21][C:3]([CH2:2][O:24][C:25]3[C:29]([CH2:30][CH:31]4[S:35][C:34](=[O:36])[N:33]([CH3:44])[C:32]4=[O:37])=[CH:28][N:27]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:26]=3)=[CH:4][C:5]=2[O:22][CH3:23])[N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 223445974-(4-Chloromethyl-2-methoxyphenoxymethyl)-2-(2-furyl)-5-methyloxazoleHCID 178518466HCID 178518466, compound

Product 1

HCID 86605785HCID 86605785, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-2-(2-furyl)-5-methyl-1,3-oxazole (0.40 g), 5-[(3-hydroxy-1-phenyl-1H-pyrazol-4-yl)methyl]-1,3-thiazolidine-2,4-dione (0.30 g) and N,N-dimethylformamide (10 mL) was added sodium hydride (60% in oil, 0.050 g) at room temperature. The mixture was stirred at room temperature for 15 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 5-({3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}methyl)-3-methyl-1,3-thiazolidine-2,4-dione as pale-yellow crystals (0.22 g, yield 37%) from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 111-112° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1df36b6b888048118c9f9de20c24dd20
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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