4-[2-(N'-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoyl}-hydrazino)-2-oxo-ethyl]-benzoic Acid Methyl Ester → 4-(5-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-phenyl}-[1,3,4]oxadiazol-2-ylmethyl)-benzoic Acid Methyl Ester

HRID 349450Notes

Reaction equation

HRID 349450 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][NH:14][C:15](=O)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[O:23][C:24]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)=[CH:25][N:26]=3)[CH:17]=2)=[O:12])=[CH:6][CH:5]=1>O>[CH3:1][O:2][C:3](=[O:36])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[O:12][C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[O:23][C:24]([C:27]5[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=5)=[CH:25][N:26]=4)[CH:17]=3)=[N:14][N:13]=2)=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 588048614-[2-(N'-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoyl}-hydrazino)-2-oxo-ethyl]-benzoic Acid Methyl Ester

Product 1

HCID 588048584-(5-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-phenyl}-[1,3,4]oxadiazol-2-ylmethyl)-benzoic Acid Methyl EsterYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.24 g (0.49 mmol) of 4-[2-(N′-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoyl}-hydrazino)-2-oxo-ethyl]-benzoic acid methyl ester from Preparation 8 was dissolved in about 10 mL of poly phosphoric acid. The mixture was stirred at 90–100° C. for 1 hour before allowing to cool to room temperature. Water was added and the product was extracted with 1:1:1 EtOAC/THF/Et2O (2×). The extracts were combined and washed with saturated aqueous NaCl solution then dried MgSO4. Slurried solid product in hot EtOAc and filtered. Dried in vacuum oven overnight at 70° C. to obtain 0.13 g (57%) desired product.

Workup

  1. extractionthe product was extracted with 1:1:1 EtOAC/THF/Et2O (2×)
  2. washwashed with saturated aqueous NaCl solution
  3. filtrationSlurried solid product in hot EtOAc and filtered
  4. customDried in vacuum oven overnight at 70° C.

Sources & evidence

ORD record
ord-3b6de6f677a34429bc2777190a5a93f2
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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