Pyridine → 5-{4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-3H-[1,3,4]oxadiazol-2-one

HRID 2103425Notes

Reaction equation

HRID 2103425 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[S:5][C:6]=1[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([NH:15][NH2:16])=[O:14])=[CH:11][CH:10]=1.[C:29]1([O:35]C(Cl)=O)C=CC=CC=1.N1C=CC=CC=1.C1CCN2C(=NCCC2)CC1>ClCCl.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][CH:20]=2)[S:5][C:6]=1[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[O:14][C:29](=[O:35])[NH:16][N:15]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 578043044-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzoic acid hydrazide

Product 1

HCID 116044505-{4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-3H-[1,3,4]oxadiazol-2-oneYield 21.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzoic acid hydrazide (Example 8, 271 mg, 0.74 mmol) in dichloromethane (7 mL) add phenylchloroformate (94 μL, 0.75 mmol) followed by pyridine (132 μL, 1.63 mmol). Stir the resulting mixture at room temperature until all the starting material is consumed (by TLC analysis). Concentrate the mixture, and then take the residue up in acetonitrile (10 mL). To this mixture, add DBU (220 μL, 1.5 mmol). Seal the resulting solution; warm it to 180° C. in a Personal Chemistry™ microwave oven and stir at this temperature for 15 min. Cool the reaction to room temperature, dilute with ethyl acetate, wash with 1 M HCl solution (or saturated NaH2PO4 solution) dry over MgSO4 and concentrate. Triturate the resulting residue with dichloromethane several times to give the title compound as a tan solid (69 mg).

Workup

  1. customis consumed (by TLC analysis)
  2. concentrationConcentrate the mixture
  3. customSeal the resulting solution
  4. temperaturewarm it to 180° C. in a Personal Chemistry™ microwave oven
  5. stirringstir at this temperature for 15 min
  6. temperatureCool
  7. customthe reaction to room temperature
  8. washwash with 1 M HCl solution (or saturated NaH2PO4 solution)
  9. dry with materialdry over MgSO4
  10. concentrationconcentrate
  11. customTriturate the resulting residue with dichloromethane several times

Sources & evidence

ORD record
ord-ec916a03ce154a2c8369f331af37f7ed
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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